1-(3-Chlorophenyl)piperazine → HCID 19810680, compound

HRID 373588Notes

Reaction equation

HRID 373588 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Br[CH2:15][CH2:16][CH2:17][NH:18][C:19]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH2:15][CH2:16][CH2:17][NH:18][C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 13551-(3-Chlorophenyl)piperazineHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2565813-Bromo-N-trityl-1-propanamine

Product 1

HCID 19810680HCID 19810680, compoundYield 105.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5.9 g (30 mmol) of 1-(3-chlorophenyl)piperazine, 12.55 g (33 mmol) of 3-bromo-N-(triphenylmethyl)propanamine, 6.2 g (45 mmol) of potassium carbonate and 60 ml of dimethylformamide is stirred at 90° C. for 6.5 h under argon. The mixture is then poured into iced water and is extracted with ethyl acetate. The organic phase is separated off, is washed with water, is dried and the solvent is evaporated off. 15.7 g of oily residue are obtained and are purified by chromatography on a column of silica gel by eluting with a 99/1 dichloromethane/methanol mixture, which yields 11.8 g of light yellow oil.

Workup

  1. extractionis extracted with ethyl acetate
  2. customThe organic phase is separated off
  3. washis washed with water
  4. customis dried
  5. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-e3c920a3bcb142418c69e20935593b80
Source dataset
uspto-grants-1992_11
Patent number
US05164397

Reaction notes

Loading…