4-Chlorobenzaldehyde → N-(4-chlorobenzyl)-3-(2,4-dimethylimidazol-1-yl)propylamine dihydrochloride

HRID 1078375Notes

Reaction equation

HRID 1078375 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][N:14]1[CH:18]=[C:17]([CH3:19])[N:16]=[C:15]1[CH3:20].[BH4-].[Na+]>C(O)C>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:10][CH2:11][CH2:12][CH2:13][N:14]2[CH:18]=[C:17]([CH3:19])[N:16]=[C:15]2[CH3:20])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 4311764Sodium borohydrideHCID 135889102,4-dimethyl-1H-imidazole-1-propanamine

Product 1

HCID 19429494N-(4-chlorobenzyl)-3-(2,4-dimethylimidazol-1-yl)propylamine dihydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a similar manner to Example 35, a mixture of 4-chlorobenzaldehyde (3.8 g) and 1-(3-aminopropyl)-2,4-dimethylimidazole (4.1 g) in ethanol (70 ml) was stirred and then reduced with sodium borohydride (2.0 g). The hydrochloride salt was triturated with propan-2-ol, filtered and the residue washed with ether, then dried under vacuum at 45° C., to give N-(4-chlorobenzyl)-3-(2,4-dimethylimidazol-1-yl)propylamine dihydrochloride, m.p. 208°-210° C.

Workup

  1. customThe hydrochloride salt was triturated with propan-2-ol
  2. filtrationfiltered
  3. washthe residue washed with ether
  4. customdried under vacuum at 45° C.

Sources & evidence

ORD record
ord-fb8b2f78d35149e8bae6f84980b283f4
Source dataset
uspto-grants-1996_08
Patent number
US05547972

Reaction notes

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