Sodium Hydroxide → N-(4-chlorophenyl)-4-hydroxy-N-[1-(1-methylethyl)-4-piperidinyl]benzeneacetamide monohydrochloride

HRID 2049084ノート

反応式

HRID 2049084 の反応式
C(=O)([O-])OCC[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([N:14]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[CH:15]2[CH2:20][CH2:19][N:18]([CH:21]([CH3:23])[CH3:22])[CH2:17][CH2:16]2)=[O:13])=[CH:7][CH:6]=1.[OH-:33].[Na+]>C(O)(=O)C>[ClH:30].[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([N:14]([CH:15]2[CH2:16][CH2:17][N:18]([CH:21]([CH3:22])[CH3:23])[CH2:19][CH2:20]2)[C:12](=[O:13])[CH2:11][C:8]2[CH:9]=[CH:10][C:5]([OH:33])=[CH:6][CH:7]=2)=[CH:25][CH:26]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 86736567{4-[2-{(4-Chlorophenyl)[1-(1-methylethyl)-4-piperidinyl]amino}-2-oxoethyl]phenyl}ethyl carbonate

生成物 1

HCID 23338991N-(4-chlorophenyl)-4-hydroxy-N-[1-(1-methylethyl)-4-piperidinyl]benzeneacetamide monohydrochloride

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
45 °C

実験手順

A mixture of 5.5 parts of {4-[2-{(4-chlorophenyl)[1-(1-methylethyl)-4-piperidinyl]amino}-2-oxoethyl]phenyl}ethyl carbonate and 50 parts of a sodium hydroxide solution 10% is stirred for 90 minutes at 45° C. The reaction mixture is cooled to room temperature and acidified with acetic acid to pH 5.5-6. The product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The oily residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (80:20 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The oily residue is converted into the hydrochloride salt in 4-methyl-2-pentanone. The salt is filtered off and dried in vacuo for 12 hours at 60° C., yielding 1.9 parts of N-(4-chlorophenyl)-4-hydroxy-N-[1-(1-methylethyl)-4-piperidinyl]benzeneacetamide monohydrochloride; mp. 242.9° C.

後処理

  1. temperatureThe reaction mixture is cooled to room temperature
  2. extractionThe product is extracted with trichloromethane
  3. customThe extract is dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe oily residue is purified by column-chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (80:20 by volume) as eluent
  8. customThe pure fractions are collected
  9. customthe eluent is evaporated
  10. filtrationThe salt is filtered off
  11. customdried in vacuo for 12 hours at 60° C.

出典と根拠

ORDレコード
ord-0bfaada263814ee0a274f2a1ec0dd8fb
出典データセット
uspto-grants-1980_04
特許番号
US04196210

反応ノート

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