Diisopropylamine → N-[1-(1-benzoylethyl)-4-(methoxymethyl)-4-piperidinyl]-N-phenylpropanamide

HRID 1448323Notes

Reaction equation

HRID 1448323 reaction equation
Br[CH:2]([CH3:11])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[CH3:12][O:13][CH2:14][C:15]1([N:21]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:22](=[O:25])[CH2:23][CH3:24])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.CC(NC(C)C)C>CC(C)CC(=O)C>[C:3]([CH:2]([N:18]1[CH2:19][CH2:20][C:15]([N:21]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:22](=[O:25])[CH2:23][CH3:24])([CH2:14][O:13][CH3:12])[CH2:16][CH2:17]1)[CH3:11])(=[O:4])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 164522-BromopropiophenoneHCID 162172Noralfentanil

Product 1

HCID 12298105N-[1-(1-benzoylethyl)-4-(methoxymethyl)-4-piperidinyl]-N-phenylpropanamide

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 3.6 parts of 2-bromo-1-phenyl-1-propanone, 4.1 parts of N-[4-(methoxymethyl)-4-piperidinyl]-N-phenylpropanamide, 3.5 parts of N-(1-methylethyl)-2-propanamine and 80 parts of 4-methyl-2-pentanone is stirred and refluxed for 16 hours. The reaction mixture is cooled to room temperature and the precipitate is filtered off. The filtrate is evaporated. The oily residue is purified by column-chromatography over silicagel, using a mixture of trichloromethane and 3% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The oily residue solidifies on triturating in petroleumether. The product is filtered off and crystallized from 2,2'-oxybispropane. It is filtered off again and dried, yielding N-[1-(1-benzoylethyl)-4-(methoxymethyl)-4-piperidinyl]-N-phenylpropanamide; mp. 123° C.

Workup

  1. temperaturerefluxed for 16 hours
  2. filtrationthe precipitate is filtered off
  3. customThe filtrate is evaporated
  4. customThe oily residue is purified by column-chromatography over silicagel
  5. additiona mixture of trichloromethane and 3% of methanol as eluent
  6. customThe pure fractions are collected
  7. customthe eluent is evaporated
  8. customon triturating in petroleumether
  9. filtrationThe product is filtered off
  10. customcrystallized from 2,2'-oxybispropane
  11. filtrationIt is filtered off again
  12. customdried

Sources & evidence

ORD record
ord-1284fef1136047cdbda002169c5582a0
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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