P-Chloroacetophenone → HCID 19429416, compound

HRID 1078374Notes

Reaction equation

HRID 1078374 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:23]=[CH:22][C:21]([C:24](=O)[CH3:25])=[CH:20][CH:19]=1.[BH4-].[Na+]>>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([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)[CH3:25])=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 7467P-ChloroacetophenoneHCID 4311764Sodium borohydrideHCID 194293864-Methyl-2-phenyl-1H-imidazole-1-propanamine

Product 1

HCID 19429416HCID 19429416, compound

Procedure

A mixture of 3-(4-methyl-2-phenylimidazol-1-yl)propyl-amine (5.3 g) and 4'-chloroacetophenone (3.8 g) was heated at 120°-125° C. for 7 hours. On cooling, the oil was dissolved in absolute alcohol (70 ml) and, after the addition of sodium borohydride (7.0 g), the mixture was boiled under reflux for 16 hours. Work-up as described in Example 3 gave an oil which was distilled at 185°-205° C. (0.06 mmHg). The main fraction was redistilled to give N-[1-(4-chlorophenyl)ethyl]-3-(4-methyl-2-phenyl-imidazol-1-yl)propylamine, b.p. 205° C. (0.04 mmHg). Glc indicated the presence of 14% of N-[1-(4-chlorophenyl)-ethyl]-3(5-methyl-2-phenylimidazol-1-yl)propylamine.

Workup

  1. temperaturewas heated at 120°-125° C. for 7 hours
  2. temperatureOn cooling
  3. temperatureunder reflux for 16 hours
  4. customgave an oil which
  5. distillationwas distilled at 185°-205° C. (0.06 mmHg)
  6. distillationThe main fraction was redistilled

Sources & evidence

ORD record
ord-d1265b1aefd9446c85066b1575ba05d4
Source dataset
uspto-grants-1996_08
Patent number
US05547972

Reaction notes

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