4-Chlorobenzaldehyde → 4-(4-Chlorophenyl)butan-1-amine

HRID 1078376Notes

Reaction equation

HRID 1078376 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[NH2:10][CH2:11][CH2:12][CH2:13]N1C=C(C)N=C1CC1C=CC=CC=1.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][CH2:13][CH2:12][CH2:11][NH2:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 4311764Sodium borohydrideHCID 194293561-(3-Aminopropyl)-2-benzyl-4-methylimidazole

Product 1

HCID 107738224-(4-Chlorophenyl)butan-1-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a similar manner to Example 35, a mixture of 4-chlorobenzaldehyde (5.6 g) and 1-(3-aminopropyl)-2-benzyl-4-methylimidazole (9.2 g) in ethanol (100 ml) was stirred and then reduced with sodium borohydride (1.6 g) to give 3-(2-benzyl-4-methylimidazol-1-yl)-[-(4-chlorobenzyl)propylamine, b.p. 190°-200° C. (0.04 mmHg). Glc and 1H nmr indicated that the product contained 21% of 3-(2-benzyl-5-methylimidazol-1-yl)-N-(4-chlorobenzyl)propylamine.

Sources & evidence

ORD record
ord-db6e93efa3e549cc86c6f1e4e07fd3eb
Source dataset
uspto-grants-1996_08
Patent number
US05547972

Reaction notes

Loading…