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

HRID 1704443노트

반응식

HRID 1704443 반응식
C(=O)(OCC)[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([N:12]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[CH:13]2[CH2:18][CH2:17][N:16]([CH:19]([CH3:21])[CH3:20])[CH2:15][CH2:14]2)=[O:11])=[CH:5][CH:4]=1.[OH-].[Na+]>C(O)(=O)C>[ClH:28].[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([N:12]([CH:13]2[CH2:18][CH2:17][N:16]([CH:19]([CH3:21])[CH3:20])[CH2:15][CH2:14]2)[C:10](=[O:11])[CH2:9][C:6]2[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=2)=[CH:23][CH:24]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 54328184{4-[2-{(4-Chlorophenyl)[1-(1-methylethyl)-4-piperidinyl]amino}-2-oxoethyl]phenyl} ethyl carbonate

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
45 °C

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-f26a83ff92814cbbb4b3bb0ac7c8b6df
출처 데이터셋
uspto-grants-1978_11
특허 번호
US04126689

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