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

HRID 26773Notes

Reaction equation

HRID 26773 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
45 °C

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-621d8a9490f242a5ad0414eceefb90ac
Source dataset
uspto-grants-1979_04
Patent number
US04151286

Reaction notes

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