2-(Aminomethyl)aniline → (5,6,7,8-Tetrahydroquinolin-8-yl)-(2-aminobenzyl)-amine

HRID 8941

반응식

HRID 8941 반응식
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].[N:10]1[C:19]2[C:18](=O)[CH2:17][CH2:16][CH2:15][C:14]=2[CH:13]=[CH:12][CH:11]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[N:10]1[C:19]2[CH:18]([NH:5][CH2:4][C:3]3[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=3[NH2:1])[CH2:17][CH2:16][CH2:15][C:14]=2[CH:13]=[CH:12][CH:11]=1

참가 물질

5

반응물 3

HCID 1780962-(Aminomethyl)anilineHCID 5049666Sodium triacetoxyborohydrideHCID 117447776,7-Dihydro-5H-quinoline-8-one

생성물 1

HCID 21985067(5,6,7,8-Tetrahydroquinolin-8-yl)-(2-aminobenzyl)-amine수율 53.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Using General Procedure B: To a solution of 2-aminobenzylamine (0.36 g, 2.9 mmol) and 6,7-dihydro-5H-quinolin-8-one (0.43 g, 2.9 mmol) in CH2Cl2 (15 mL) was added NaBH(OAc)3 (0.92 g, 4.4 mmol) and the mixture stirred at room temperature for 64 h. Purification of the crude material by column chromatography on silica gel (2% MeOH/CH2Cl2) gave (5,6,7,8-tetrahydroquinolin-8-yl)-(2-aminobenzyl)-amine (0.39 g, 52%) as a yellow oil. 1H NMR (CDCl3) δ 1.80 (m, 1H), 1.94 (m, 2H), 2.17 (m, 1H), 2.79 (m, 2H), 3.84 (m, 1H), 3.87 (d, 1H, J=11.7 Hz), 4.02 (d, 1H, J=12.0 Hz), 6.64 (d, 1H, J=7.8 Hz), 6.67 (t, 1H, J=7.8 Hz), 7.09 (m, 3H), 7.38 (d, 1H, J=3.0 Hz), 8.38 (d, 1H, J=3.9 Hz).

후처리

  1. customPurification of the crude material by column chromatography on silica gel (2% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-9ae33e70ed0a4b709b1d6590d317a032
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091217B2

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