Cis-(4-Aminocyclohexyl)methanol

Cis-(4-Aminocyclohexyl)methanol

[0526] Lithium aluminium hydride (14 ml, 1M solution in tetrahydrofuran, 14 mmol) was added dropwise to an ice-cooled solution of cis-4-aminocyclohexanecarboxylic acid (1.33 g, 9.29 mmol) in tetrahydrofuran (50 ml), and once addition was complete, the reaction was heated under reflux for 6 hours. The resulting suspension was cooled to 5° C., and water (0.6 ml), aqueous sodium hydroxide solution (1.1 ml, 2M), then water (0.6 ml) were added sequentially. The resulting suspension was filtered, and the filtrate evaporated under reduced pressure to give an oil, which was used without further purification;

 ¹H NMR (CDCl₃, 300 MHz) δ: 1.40-1.80 (m, 12H), 3.00 (m, 1H), 3.55 (d, 2H); 

LRMS: m/z 130.2 (MH⁺).

5-Amino-1-benzyl-2(1H)-pyridinone

5-Amino-1-benzyl-2(1H)-pyridinone

 A mixture of 1-benzyl-5-nitro-1H-pyridin-2-one (Justus Liebigs Ann. Chem. 484; 1930; 52) (1.0 g, 4.35 mmol), and granulated tin (3.5 g, 29.5 mmol) in concentrated hydrochloric acid (14 ml) was heated at 90° C. for 1.5 hours. The cooled solution was diluted with water, neutralised using sodium carbonate solution, and extracted with ethyl acetate (250 ml in total). The combined organic extracts were filtered, dried (MgSO₄), and evaporated under reduced pressure to give the title compound as a pale green solid, (turned blue with time), 440 mg, 51%; 

¹H NMR (CDCl₃, 250 MHz) δ: 4.12-4.47 (bs, 2H), 5.00 (s, 2H), 6.31 (d, 1H), 6.86 (s, 1H), 7.07 (m, 1H), 7.14-7.42 (m, 5H).

1-(2-Aminopropyl)-2-pyrrolidinone

1-(2-Aminopropyl)-2-pyrrolidinone

[0511] A mixture of the oxime from preparation 17 (375 mg, 2.40 mmol) and platinum oxide (300 mg) in ethanol (20 ml) was hydrogenated at 60 psi and room temperature for 18 hours. Tlc analysis showed starting material remaining, so additional platinum oxide (100 mg) was added and the reaction continued for a further 4 hours. The mixture was filtered through Arbocel®, and the filtrate evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol:0.88 ammonia (95:5:0.5 to 90:10:1) to give the title compound as a clear oil, 170 mg, 50%; 

http://www.google.com/patents/US20020052370

¹H NMR (CDCl₃, 400 MHz)

δ: 1.02 (d, 3H), 1.36 (bs, 2H), 2.00 (m, 2H), 2.38 (t, 2H), 3.00-3.16 (m, 2H), 3.21 (m, 1H), 3.35-3.45 (m, 2H); 

LRMS: m/z 143 (MH⁺).

Magnolignan C

CAS No.:93697-42-8

C₁₈H₂₀O₄, FW 300.36

UV

λmax (MeOH): 259

MASS

EIMS m/z: 300.13 [M]+

1H NMR

(300 MHz, CD3OD) δ: 2.62, 2.75 (2H, dd, J = 12, 6 Hz, H-7'), 3.31, 3.37 (2H, dd, J = 6.0 Hz, H-7), 3.50 (2H, m, H-9'), 3.79 (1H, m, H-8'), 5.00, 5.08 (2H, dd, J = 11, 18 Hz, H-9), 6.02 (1H, m, H-8), 6.77-7.25 (6H, m, Ar-H)

13C NMR

(75 MHz, CD3OD) δ: 35.4 (C-7), 40.2 (C-7'), 66.7 (C-9'), 74.8 (C-8'), 115.4 (C-9), 115.6 (C-3'), 116.9 (C-5), 127.4 (C-3), 129.3 (C-6), 129.7 (C-2), 130.0 (C-1'), 131.3 (C-5'), 131.6 (C-4'), 132.1 (C-1), 132.6 (C-6'), 138.6 (C-8), 153.5 (C-2'), 155.2 (C-4)

N-(4-amino-4′-hydroxybiphen-3-yl)-4-methoxybenzamide

 


 N-(4-amino-4′-hydroxybiphen-3-yl)-4-methoxybenzamide







Example 45

N-(4-amino-4′-hydroxybiphen-3-yl)-4-methoxybenzamide (160)

Step 1. (3-Bromophenoxy)(tert-butyl)dimethylsilane (159) Following the same procedure as in Example 19, step 2 (scheme 17) substituting compound 90 for 3-bromophenol 158 (200 mg, 0.501 mmol), the title compound 159 was obtained (14 mg, 5% yield). ¹H NMR: (400 MHz, DMSO-d₆) δ (ppm): 7.21 (t, J=8.0 Hz, 1H), 7.14 (d, J=7.8 Hz, 1H), 7.01 (s, 1H), 6.86 (d, J=8.0 Hz, 1H), 0.95 (d, J=1.0 Hz, 9H), 0.20 (d, J=1.2 Hz, 6H).
Step 2. N-(4-amino-4′-hydroxybiphen-3-yl)-4-methoxybenzamide (160) Following the same procedure as in Example 31, step 1 (scheme 21) but substituting 1-(4-bromophenyl)ethanone for compound 159 (312 mg, 1.09 mmol), the title compound 160 was obtained (79 mg, 44% yield).

 ¹H NMR: (400 MHz, DMSO-d₆) δ (ppm): 9.58 (s, 1H), 9.35 (s, 1H), 7.97 (d, J=8.4 Hz, 2H), 7.43 (s, 1H), 7.23 (dd, J=8.2, 1.4 Hz, 1H), 7.16 (t, J=7.6 Hz, 1H), 7.04 (d, J=8.4 Hz, 2H), 6.95 (d, J=7.6 Hz, 1H), 6.91 (s, 1H), 6.82 (d, J=8.4 Hz, 1H), 6.62 (dt, J=8.0, 1.0 Hz, 1H), 5.05 (s, 2H), 3.84 (s, 3H).
LRMS: (m/z): 335.2 (MH⁺).



 SEE



http://www.google.com/patents/US7868205

4-((3,4-Dimethoxyphenylamino)methyl)-N-(2-amino-5-cyanophenyl)benzamide

 


http://www.google.com/patents/US7868205

 Example 55

4-((3,4-Dimethoxyphenylamino)methyl)-N-(2-amino-5-cyanophenyl)benzamide (199)

Step 1: 4-((3,4-Dimethoxyphenylamino)methyl)-N-(2-amino-5-cyanophenyl)benzamide (199) Following the same procedure as described in Example 27, step 2 (scheme 20), the title compound 199 was obtained in 16% yield.  


¹H NMR: (DMSO)
δ (ppm): 9.56 (bs, 1H),
7.89 (d, J=8.0 Hz, 2H),
7.52 (bs, 1H),
7.45 (d, J=8.4 Hz, 2H),
6.77 (d, J=8.4 Hz, 1H),
6.63 (d, J=8.4 Hz, 1H),
6.30 (d, J=2.4 Hz, 1H),
5.99-5.95 (m, 2H),
5.74 (bs, 1H),
4.92 (bs, 2H),
3.64 (s, 3H),
3.32 (s, 3H).


MS: (calc); 402.5 (obt.) 403.4 (MH)⁺.

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Plumbagin analogs-synthesis, characterization, and antitubercular activity

Compound a

This was synthesized using above scheme. R _f 0.44 (Silica Gel G, n-hexane: EtOAc, 10:2); 

IR (cm ^-1 ) 3067 (Aromatic C-H), 2985 (Aliphatic-CH₂ ), 1678 (Aryl C = C), 1631 (C = O), 1452 (Aromatic ring stretch); 
nmr
(400 MHz, DMSO-d6), dH ppm: 2.469 (1H, s), 3.025-3.006 (4H, q, J = 7.6 Hz), 1.258-1.240 (3H, t, J = 7 Hz), 6.998 (1H, m), 7.126 (1H, m), 7.254 (1H, m), 7.468 (1H, m), 7.536 (1H, m), 7.552 (1H, m), 8.076 (1H, m), 7.969 (1H, s), 7.900 (1H, s), 8.605 (1H, s); m ⁄ z 507.13(M+).

http://www.japtr.org/article.asp?issn=2231-4040;year=2014;volume=5;issue=1;spage=28;epage=32;aulast=Nayak