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

HRID 8941Notes

Reaction equation

HRID 8941 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-9ae33e70ed0a4b709b1d6590d317a032
Source dataset
uspto-grants-2006_08
Patent number
US07091217B2

Reaction notes

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