Water → 1-Pentanone, 1-[4-(phenylamino)-1-(2-phenylethyl)-4-piperidinyl]-

HRID 1973793Notes

Reaction equation

HRID 1973793 reaction equation
[C:1]1([NH:7][C:8]2([C:22](O)=[O:23])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O(CC)CC.O.[CH3:31][CH2:32][CH2:33][CH2:34]CC>>[C:1]1([NH:7][C:8]2([C:22](=[O:23])[CH2:31][CH2:32][CH2:33][CH3:34])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:10][CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 8058HexaneHCID 6162334-Piperidinecarboxylic acid, 4-(phenylamino)-1-(2-phenylethyl)-

Product 1

HCID 122982241-Pentanone, 1-[4-(phenylamino)-1-(2-phenylethyl)-4-piperidinyl]-

Procedure

To a stirred and cooled (-5° C) suspension of 16.2 parts of 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylic acid in 525 parts of dry 1,1'-oxybisethane, are added dropwise 228.5 parts of 1-lithiumbutane solution 20% in hexane at 0° C. Upon completion, stirring is continued for 3 hours at 0° C. The reaction mixture is decomposed by addition of 300 parts of water. The organic phase is separated, washed with water, dried, filtered and evaporated. The oily residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 2.5% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The oil residue is dissolved in 2,2'-oxybispropane and the solution is stirred with activated charcoal. The latter is filtered off and the filtrate is evaporated. The residue is crystallized from petroleum-ether, yielding 1-[4-(phenylamino)-1-(2-phenylethyl)-4-piperidinyl]-1-pentanone; mp. 71.3° C.

Workup

  1. temperaturecooled
  2. stirringUpon completion, stirring
  3. customThe organic phase is separated
  4. washwashed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe oily residue is purified by column-chromatography over silica gel using
  9. additiona mixture of trichloromethane and 2.5% of methanol as eluent
  10. customThe pure fractions are collected
  11. customthe eluent is evaporated
  12. dissolutionThe oil residue is dissolved in 2,2'-oxybispropane
  13. stirringthe solution is stirred with activated charcoal
  14. filtrationThe latter is filtered off
  15. customthe filtrate is evaporated
  16. customThe residue is crystallized from petroleum-ether

Sources & evidence

ORD record
ord-e4d6faa430904f95a257acfe045df281
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

Loading…