Dichloromethane → N-[alpha-(4-chlorophenyl)benzyl]-3-(imidazol-1-yl)propylamine

HRID 1078369Notes

Reaction equation

HRID 1078369 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=O)=[CH:4][CH:3]=1.[NH2:16][CH2:17][CH2:18][CH2:19][N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1.[BH4-].[Na+].ClCCl>C(O)C>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH:6]([NH:16][CH2:17][CH2:18][CH2:19][N:20]2[CH:24]=[CH:23][N:22]=[CH:21]2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 86534-ChlorobenzophenoneHCID 787361H-Imidazole-1-propanamineHCID 4311764Sodium borohydride

Product 1

HCID 19429460N-[alpha-(4-chlorophenyl)benzyl]-3-(imidazol-1-yl)propylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
130 °C

Procedure

In a similar manner to Example 1, a mixture of 4-chlorobenzophenone (8.0 g) and 1-(3-aminopropyl)imidazole (4.6 g) was heated at 130° C. for 12 hours. The mixture was cooled, dissolved in absolute ethanol (100 ml), treated with sodium borohydride (2.8 g) and the mixture boiled under reflux for 8 hours. The oil obtained after work-up, using dichloromethane as the extracting solvent, was distilled to give N-[α-(4-chlorophenyl)benzyl]-3-(imidazol-1-yl)propylamine, b.p. 240° C. (0.3 mmHg).

Workup

  1. temperatureThe mixture was cooled
  2. temperatureunder reflux for 8 hours
  3. customThe oil obtained after work-up
  4. distillationwas distilled

Sources & evidence

ORD record
ord-7f6f58dd95974ae2a26019a100138f87
Source dataset
uspto-grants-1996_08
Patent number
US05547972

Reaction notes

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