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

HRID 28164Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 28164
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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

A mixture of 5.5 parts of {4-[2-{(4-chlorophenyl)[1-(1-methylethyl)-4-piperidinyl-]amino}-2-oxoethyl]phenyl}ethyl carbonate and 5 C 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.

Aufarbeitung

  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.

Quellen und Nachweise

ORD-Eintrag
ord-3717e96f57d242e1aad98eef2a47bc00
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04225606

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