Water → HCID 12298069, compound

HRID 1448313Notes

Reaction equation

HRID 1448313 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[O:10]=[C:11]([N:14]([C:21]1([C:27]([O:29][CH2:30][CH2:31][CH3:32])=[O:28])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:12][CH3:13].C(N(CC)CC)C.CN(C)C(=[O:44])C.[OH2:46]>>[C:27]([OH:29])(=[O:28])[C:21]([OH:44])=[O:46].[O:10]=[C:11]([N:14]([C:21]1([C:27]([O:29][CH2:30][CH2:31][CH3:32])=[O:28])[CH2:26][CH2:25][N:24]([CH2:2][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:12][CH3:13]

Participants

6

Reactant 5

HCID 962WaterHCID 7666Phenethyl bromideHCID 8471TriethylamineHCID 31374DimethylacetamideHCID 12298183HCID 12298183, compound

Product 1

HCID 12298069HCID 12298069, compound

Procedure

A mixture of 3.34 parts of (2-bromoethyl)benzene, 4.80 parts of propyl 4-[N-(1-oxopropyl)-N-phenylamino]-4-piperidinecarboxylate, 2.02 parts of N,N-diethylethanamine and 81 parts of N,N-dimethylacetamide is stirred and heated for 3 hours at 70°-80° C. The reaction mixture is cooled and poured onto 400 parts of water. The product is extracted with 1,1'-oxybisethane. The extract is washed with water, dried, filtered and evaporated. The oily residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 15% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The residue is converted into the ethanedioate salt in 2-propanone, yielding propyl 4-[N-(1-oxopropyl)-N-phenylamino]-1-(2-phenylethyl)-4-piperidinecarboxylate ethanedioate; mp. 215.7° C.

Workup

  1. temperatureheated for 3 hours at 70°-80° C
  2. temperatureThe reaction mixture is cooled
  3. extractionThe product is extracted with 1,1'-oxybisethane
  4. washThe extract is washed 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 15% of methanol as eluent
  10. customThe pure fractions are collected
  11. customthe eluent is evaporated

Sources & evidence

ORD record
ord-8bc004007bd64acf9f78c8afec58483f
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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