Triethylamine → 1-[Bis(4-fluorophenyl)methyl]-4-(2,3,4-trimethoxycinnamoyl)piperazine hydrochloride

HRID 256480

反応式

HRID 256480 の反応式
[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.[F:22][C:23]1[CH:28]=[CH:27][C:26]([CH:29]([N:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)[C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)=[CH:25][CH:24]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.C(Cl)Cl>[ClH:20].[F:36][C:33]1[CH:32]=[CH:31][C:30]([CH:29]([C:26]2[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=2)[N:37]2[CH2:38][CH2:39][N:40]([C:7](=[O:9])[CH:6]=[CH:5][C:4]3[CH:10]=[CH:11][C:12]([O:16][CH3:17])=[C:13]([O:14][CH3:15])[C:3]=3[O:2][CH3:1])[CH2:41][CH2:42]2)=[CH:35][CH:34]=1

参加物

8

反応物 5

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 1184003-(2,3,4-Trimethoxyphenyl)-2-propenoic acidHCID 1529321-(Bis(4-fluorophenyl)methyl)piperazineHCID 516892Sodium Bicarbonate

生成物 1

HCID 679325131-[Bis(4-fluorophenyl)methyl]-4-(2,3,4-trimethoxycinnamoyl)piperazine hydrochloride収率 27.3%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

実験手順

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 2.7 g (9.4 millimoles) of bis(4-fluorophenyl)methylpiperazine and 2 g (19.8 millimoles) of triethylamine. The mixture was stirred for 30 minutes under ice cooling. Thereafter, 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 methanol gave 1.4 g (yield 27.3%) of 1-[bis(4-fluorophenyl)methyl]-4-(2,3,4-trimethoxycinnamoyl)piperazine hydrochloride as colorless crystals.

後処理

  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 methanol

出典と根拠

ORDレコード
ord-23e8de526bdb4db08fd835324bfaa500
出典データセット
uspto-grants-1987_10
特許番号
US04703048

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