P-Chloroacetophenone → N-[1-(4-chlorophenyl)ethyl]-3-(2,4-dimethylimidazol-1-yl)propylamine dihydrochloride

HRID 1078373Notes

Reaction equation

HRID 1078373 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[CH:4][CH:3]=1.[NH2:11][CH2:12][CH2:13][CH2:14][N:15]1[CH:19]=[C:18]([CH3:20])[N:17]=[C:16]1[CH3:21].[BH4-].[Na+]>C(O)C>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:11][CH2:12][CH2:13][CH2:14][N:15]2[CH:19]=[C:18]([CH3:20])[N:17]=[C:16]2[CH3:21])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7467P-ChloroacetophenoneHCID 4311764Sodium borohydrideHCID 135889102,4-dimethyl-1H-imidazole-1-propanamine

Product 1

HCID 19429532N-[1-(4-chlorophenyl)ethyl]-3-(2,4-dimethylimidazol-1-yl)propylamine dihydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a similar manner to Example 1, a mixture of 4'-chloroacetophenone (4.0 g) and 1-(3-aminopropyl)-2,4-dimethylimidazole (4.0 g) was heated at 115°-120° C. for 7 hours then reduced with sodium borohydride (2.0 g) in ethanol (70 ml) over 18 hours. The solid obtained was triturated with propan-2-ol and filtered to give N-[1-(4-chlorophenyl)ethyl]-3-(2,4-dimethylimidazol-1-yl)propylamine dihydrochloride, m.p. 218°-220° C.

Workup

  1. temperaturewas heated at 115°-120° C. for 7 hours
  2. customThe solid obtained
  3. customwas triturated with propan-2-ol
  4. filtrationfiltered

Sources & evidence

ORD record
ord-2671ebec801b435e9eafb03be4b036bf
Source dataset
uspto-grants-1996_08
Patent number
US05547972

Reaction notes

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