Acetic Acid → methyl [1-{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-1H-benzimidazol-2-yl]carbamate

HRID 2050316ノート

反応式

HRID 2050316 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][N:15]([CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14][CH2:13]1.N=CO[CH2:34][NH:35][C:36](=[O:39])[O:37][CH3:38].C(O)(=O)C>ClC(Cl)Cl>[CH3:38][O:37][C:36](=[O:39])[NH:35][C:34]1[N:8]([CH2:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][N:15]([CH:18]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:16][CH2:17]2)[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=1

参加物

5

反応物 3

HCID 176Acetic AcidHCID 13105609N~1~-{3-[4-(Diphenylmethyl)piperazin-1-yl]propyl}benzene-1,2-diamineHCID 15037334Methyl (iminomethoxymethyl)-carbamate

生成物 1

HCID 13105584methyl [1-{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-1H-benzimidazol-2-yl]carbamate

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

A mixture of 60 parts of N-(2-aminophenyl)-4-(diphenylmethyl)-1-piperazinepropanamine, 20 parts of methyl (iminomethoxymethyl)carbamate, 42 parts of acetic acid and 450 parts of trichloromethane is stirred and refluxed overnight. The reaction mixture is evaporated and the residue is stirred in water. The latter is decanted and the residue is taken up again in water. The whole is alkalized with a diluted ammonium hydroxide solution and the product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane, yielding methyl[1-{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-1H-benzimidazol-2-yl]carbamate; mp. 137.8° C.

後処理

  1. temperaturerefluxed overnight
  2. customThe reaction mixture is evaporated
  3. stirringthe residue is stirred in water
  4. customThe latter is decanted
  5. extractionthe product is extracted with trichloromethane
  6. customThe extract is dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is purified by column-chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  11. customThe pure fractions are collected
  12. customthe eluent is evaporated
  13. customThe residue is crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane

出典と根拠

ORDレコード
ord-a0dec1d9087944d0a7f11cba5f50caf2
出典データセット
uspto-grants-1980_04
特許番号
US04200641

反応ノート

読み込み中…