Benzaldehyde → N-(1H-benzimidazol-2-ylmethyl)-N-[[4-[(benzylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine

HRID 7156

Reaction equation

HRID 7156 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[CH2:18][N:19]([CH:29]1[C:38]2[N:37]=[CH:36][CH:35]=[CH:34][C:33]=2[CH2:32][CH2:31][CH2:30]1)[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH2:28])=[CH:23][CH:22]=1.[BH4-].[Na+]>CO>[CH2:1]([NH:28][CH2:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:19]([CH2:18][C:10]2[NH:9][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=2)[CH:29]2[C:38]3[N:37]=[CH:36][CH:35]=[CH:34][C:33]=3[CH2:32][CH2:31][CH2:30]2)=[CH:22][CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 4311764Sodium borohydrideHCID 21985008N-[(1H-Benzo[d]imidazol-2-yl)methyl]-N-(4-(aminomethyl)-benzyl)-5,6,7,8-tetrahydroquinolin-8-amine

Product 1

HCID 22018607N-(1H-benzimidazol-2-ylmethyl)-N-[[4-[(benzylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amineYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Benzaldehyde (0.5 mL, 4.92 mmol) was condensed with N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (170 mg, 0.428 mmol) in dry MeOH (3 mL) for 17 h at room temperature and the resultant imine was reduced with sodium borohydride (329 mg, 8.70 mmol) for 1 h (see General Procedures A and B). Purification of the crude product by flash chromatography (14 g silica, 30:1:1 EtOAc/CH3OH/NH4OH) followed by radial chromatography (2 mm TLC plate, 100:1:1 CH2Cl2/CH3OH/NH4OH) gave the N-alkylated product (54 mg, 26%) as a foam.

Workup

  1. customPurification of the crude product by flash chromatography (14 g silica, 30:1:1 EtOAc/CH3OH/NH4OH)

Sources & evidence

ORD record
ord-3b54507cbfb14b84b0322c01958b4f77
Source dataset
uspto-grants-2006_08
Patent number
US07084155B2

Linked notes

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