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

HRID 8941ノート

反応式

HRID 8941 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-9ae33e70ed0a4b709b1d6590d317a032
出典データセット
uspto-grants-2006_08
特許番号
US07091217B2

反応ノート

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