Triethylamine → 1-(3-Acetylaminobenzoyl)-4-[2-(4-chlorophenyl)ethyl]piperazine

HRID 1381884

反応式

HRID 1381884 の反応式
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=O)(=[O:3])[CH3:2].C(N(CC)CC)C.C(OC(Cl)=O)C.[Cl:27][C:28]1[CH:41]=[CH:40][C:31]([CH2:32][CH2:33][N:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)=[CH:30][CH:29]=1>CN(C=O)C.C(Cl)Cl>[Cl:27][C:28]1[CH:41]=[CH:40][C:31]([CH2:32][CH2:33][N:34]2[CH2:35][CH2:36][N:37]([C:8](=[O:10])[C:7]3[CH:11]=[CH:12][CH:13]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:6]=3)[CH2:38][CH2:39]2)=[CH:30][CH:29]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 488473-Acetamidobenzoic acidHCID 122357141-[2-(4-Chlorophenyl)ethyl]piperazine

生成物 1

HCID 190995361-(3-Acetylaminobenzoyl)-4-[2-(4-chlorophenyl)ethyl]piperazine

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

10 g of 3-acetamidobenzoic acid are dissolved in 100 ml of DMF. At a temperature of from -5° to 0° there are added dropwise, while stirring, firstly 5.65 g of triethylamine and then 6.05 g of chloroformic acid ethyl ester dissolved in 40 ml of CH2Cl2. The whole is stirred for a further 30 minutes at from 0° to +5° and then, at the same temperature, 12.54 g of 1-(p-chlorophenethyl)piperazine in 75 ml of DMF are added dropwise. The whole is stirred overnight at room temperature and then concentrated to dryness by evaporation. The residue is taken up in 350 ml of CH2Cl2 and the whole is washed with 150 ml of 2N NaOH and with 50 ml of H2O and dried over Na2SO4. After filtration and concentration by evaporation, a brown oil is obtained, which is caused to crystallise with ether. Recrystallisation is effected from ethanol/ether. 1-[2-(p-chlorophenyl)-ethyl]-4-(3-acetamidobenzoyl)-piperazine having a melting point of 101°-107° is thus obtained.

後処理

  1. additionAt a temperature of from -5° to 0° there are added dropwise
  2. stirringThe whole is stirred for a further 30 minutes at from 0° to +5°
  3. stirringThe whole is stirred overnight at room temperature
  4. concentrationconcentrated to dryness by evaporation
  5. washthe whole is washed with 150 ml of 2N NaOH and with 50 ml of H2O
  6. dry with materialdried over Na2SO4
  7. filtrationAfter filtration and concentration
  8. customby evaporation
  9. customa brown oil is obtained
  10. customto crystallise with ether
  11. customRecrystallisation

出典と根拠

ORDレコード
ord-93c2324ff7574cbdb668543b2741734c
出典データセット
uspto-grants-1989_02
特許番号
US04804661

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