4-Chlorobenzaldehyde → HCID 19429422, compound

HRID 1078377Notes

Reaction equation

HRID 1078377 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:5]([CH2:7][CH2:8][CH2:9][NH2:10])[CH:6]=1.[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1.[BH4-].[Na+]>C(O)C>[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH:10][CH2:9][CH2:8][CH2:7][N:5]2[CH:6]=[C:2]([CH3:1])[N:3]=[C:4]2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 4311764Sodium borohydrideHCID 194293864-Methyl-2-phenyl-1H-imidazole-1-propanamine

Product 1

HCID 19429422HCID 19429422, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(4-Methyl-2-phenylimidazol-1-yl)propylamine (5.5 g) and 4-chlorobenzaldehyde (3.6 g) were stirred in absolute ethanol (70 ml) for 16 hours. Sodium borohydride (2.0 g) was added and the mixture heated under reflux for 7 hours. Work-up as described in Example 42 gave N-(4-chlorobenzyl)-3-(4-methyl-2-phenylimidazol-1-yl)propylamine. Glc indicated that the product contained 13% (approx) of N-(4-chlorobenzyl)-3(5-methl-2-phenylimidazol-1-yl)propylamine.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 7 hours

Sources & evidence

ORD record
ord-4ae285ae2f93489b98cdb962c39b5917
Source dataset
uspto-grants-1996_08
Patent number
US05547972

Reaction notes

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