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Methyl Isobutyl Ketone → N-[1-(2-phenylethyl)-4-piperidinyl]-1-[2-(2-thienyl)ethyl]-1H-benzimidazol-2-amine

HRID 1856569
ノート
印刷プレビュー

反応式

HRID 1856569 の反応式
[C:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([NH:15][C:16]3[NH:20][C:19]4[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=4[N:17]=3)[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC1C=CC(S(O[CH2:36][CH2:37][C:38]2[S:39][CH:40]=[CH:41][CH:42]=2)(=O)=O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+].CC(C)CC(=O)C>O>[C:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([NH:15][C:16]3[N:17]([CH2:36][CH2:37][C:38]4[S:39][CH:40]=[CH:41][CH:42]=4)[C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 36820342-Thiopheneethanol tosylateHCID 12891523N-[1-(2-Phenylethyl)piperidin-4-yl]-1H-benzimidazol-2-amine

生成物 1

HCID 12891721N-[1-(2-phenylethyl)-4-piperidinyl]-1-[2-(2-thienyl)ethyl]-1H-benzimidazol-2-amine収率 23.2%

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

実験手順

A mixture of 3.2 parts of N-[1-(2-phenylethyl)-4-piperidinyl]-1H-benzimidazol-2-amine, 2.9 parts of [2-(2-thienyl)ethyl] 4-methylbenzenesulfonate, 1 part of sodium carbonate and 135 parts of 4-methyl-2-pentanone is stirred and refluxed overnight with water-separator. The reaction mixture is poured onto water and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from a mixture of 2,2'-oxybispropane and 2-propanone, yielding 1 part (23.2%) of N-[1-(2-phenylethyl)-4-piperidinyl]-1-[2-(2-thienyl)ethyl]-1H-benzimidazol-2-amine; mp. 118.3° C.

後処理

  1. additionThe reaction mixture is poured onto water
  2. customthe layers are separated
  3. customThe organic phase is dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by column-chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  8. customThe pure fractions are collected
  9. customthe eluent is evaporated
  10. customThe residue is crystallized from a mixture of 2,2'-oxybispropane and 2-propanone

出典と根拠

ORDレコード
ord-85e86dae2d544bd2901faccba6cb8981
出典データセット
uspto-grants-1980_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04219559

反応ノート

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