Triethylamine → 1-Benzhydryl-4-(2,3,4-trimethoxycinnamoyl)piperazine hydrochloride

HRID 256481Notes

Reaction equation

HRID 256481 reaction equation
[CH3:1][O:2][C:3]1[C:13]([O:14][CH3:15])=[C:12]([O:16][CH3:17])[CH:11]=[CH:10][C:4]=1[CH:5]=[CH:6][C:7]([OH:9])=O.S(Cl)([Cl:20])=O.[CH:22]([N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.C(Cl)Cl>[ClH:20].[CH:22]([N:35]1[CH2:40][CH2:39][N:38]([C:7](=[O:9])[CH:6]=[CH:5][C:4]2[CH:10]=[CH:11][C:12]([O:16][CH3:17])=[C:13]([O:14][CH3:15])[C:3]=2[O:2][CH3:1])[CH2:37][CH2:36]1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 70048BenzhydrylpiperazineHCID 1184003-(2,3,4-Trimethoxyphenyl)-2-propenoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 679325361-Benzhydryl-4-(2,3,4-trimethoxycinnamoyl)piperazine hydrochlorideYield 43.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

In 10 ml of chloroform was suspended 2.5 g (10.5 millimoles) of 2,3,4-trimethoxycinnamic acid, and under ice cooling, 3.5 ml (about 48 millimoles) of thionyl chloride was added dropwise. The mixture was stirred for 30 minutes under ice cooling, and the excess of thionyl chloride and chloroform were distilled off under reduced pressure. The residue was diluted with 20 ml of methylene chloride, and added dropwise under ice cooling to 30 ml of a methylene chloride solution of 2.5 g (9.9 millimoles) of benzhydrylpiperazine and 2 g (19.8 millimoles) of triethylamine. The mixture was stirred for 30 minutes under ice cooling. A 10% aqueous solution of sodium bicarbonate was added, and the mixture was shaken. The organic layer was separated, washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The resulting oily product was diluted with 20 ml of ethanol. One milliliter of concentrated hydrochloric acid was added, and then ether was added. The crystals that precipitated were collected by filtration. Recrystallization from ethanol gave 2.2 g (yield 43.7%)of 1-benzhydryl-4-(2,3,4-trimethoxycinnamoyl)piperazine hydrochloride as colorless crystals.

Workup

  1. distillationthe excess of thionyl chloride and chloroform were distilled off under reduced pressure
  2. additionThe residue was diluted with 20 ml of methylene chloride
  3. stirringThe mixture was stirred for 30 minutes under ice cooling
  4. stirringthe mixture was shaken
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. additionThe resulting oily product was diluted with 20 ml of ethanol
  10. additionOne milliliter of concentrated hydrochloric acid was added
  11. additionether was added
  12. customThe crystals that precipitated
  13. filtrationwere collected by filtration
  14. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-7c2b4d441453427fb8b1769d733468a2
Source dataset
uspto-grants-1987_10
Patent number
US04703048

Reaction notes

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