Thionyl Chloride → HCID 13753408, compound

HRID 2290283Notes

Reaction equation

HRID 2290283 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]=[CH:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH:7](O)[C:6]=2[CH:17]=1.S(Cl)([Cl:20])=O>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]=[CH:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH:7]([Cl:20])[C:6]=2[CH:17]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 13753407HCID 13753407, compound

Product 1

HCID 13753408HCID 13753408, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

663 milligrams (2.31 millimoles) of 3-bromo-5H-dibenzo[a,d]cyclohepten-5-ol, 825 milligrams (6.94 millimoles) of thionyl chloride and 10 milliliters of benzene were mixed together and refluxed for 1.5 hours and the solvent removed in vacuo to obtain a 3-bromo-5-chloro-5H-dibenzo[a,d]-cycloheptene product as residue. The residue was dissolved in 10 milliliters of dimethylformamide and 1.74 milliliters (1.29 grams, 10.0 millimoles) of ethyl diisopropyl amine and 500 milligrams (2.31 millimoles) of cinnamoylpiperazine added thereto and the resulting mixture stirred overnight to obtain a 1-(3-bromo-5H-dibenzo[a,d]cyclohepten-5-yl)-4-cinnamoylpiperazine compound in the reaction mixture. It was recovered as residue by vaporizing the solvent in vacuo, the residue then was dissolved in ethyl acetate, the ethyl acetate solution washed with three 50 milliliter portions of water and with one 100 milliliter portion of brine, and then dried over potassium carbonate. After removing the drying agent, the solvent was evaporated in vacuo from the dried solution to obtain 1.07 grams (95 percent yield) of the cinnamoylpiperazine compound.

Workup

  1. temperaturerefluxed for 1.5 hours
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-769e517c32de4137a88aef0ed974f2e8
Source dataset
uspto-grants-1986_10
Patent number
US04616023

Reaction notes

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