Acetonitrile → 1-(3-Chloro-5-trifluoromethyl-phenyl)-4-propyl-piperazine

HRID 584049Notes

Reaction equation

HRID 584049 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[C:18]([O-])([O-])=O.[K+].[K+].[CH3:24][C:25]#N>>[Cl:1][C:2]1[CH:3]=[C:4]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:25][CH3:24])[CH2:14][CH2:13]2)[CH:5]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:7]=1

Participants

4

Reactant 3

HCID 6342Acetonitrile2×HCID 11430Potassium CarbonateHCID 223451951-(3-Chloro-5-(trifluoromethyl)phenyl)piperazine

Product 1

HCID 98577261-(3-Chloro-5-trifluoromethyl-phenyl)-4-propyl-piperazine

Conditions

Temperature
50 °C

Procedure

A suspension of 1-(3-Chloro-5-trifluoromethyl-phenyl)-piperazine (100 mg) and ground K2CO3 (200 mg) was stirred in CH3CN (30 mL) at room temperature. A solution of 1-bromo-propyl (52 mg) in CH3CN (5 mL) was added dropwise. The mixture was stirred at 50° C. overnight. The reaction mixture was filtered and the volatiles were evaporated in vacuum. The oily residue was chromatographed on a silica column with MeOH: CH2Cl2 (1:9 (v/v)) as eluent. Collection of the fractions containing pure product and evaporation of the solvent afforded the title compound (85 mg). MS m/z (relative intensity, 70 eV) 306 (M+, 25), 277 (bp), 234 (23), 206 (23), 179 (23).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe volatiles were evaporated in vacuum
  3. customThe oily residue was chromatographed on a silica column with MeOH: CH2Cl2 (1:9 (v/v)) as eluent
  4. customCollection of the fractions
  5. additioncontaining pure
  6. customproduct and evaporation of the solvent

Sources & evidence

ORD record
ord-83300e617b1e43b39110562d9603024c
Source dataset
uspto-grants-2005_08
Patent number
US06924374B2

Reaction notes

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