Sodium Carbonate → HCID 12298063, compound

HRID 1973820Notes

Reaction equation

HRID 1973820 reaction equation
[CH3:1][CH:2](O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[O:11]=[C:12]([N:15]([C:22]1([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:13][CH3:14].[C:33](=[O:36])([O-:35])[O-].[Na+].[Na+]>CC(C)CC(=O)C>[C:28]([OH:30])(=[O:29])[C:33]([OH:35])=[O:36].[CH3:1][CH:2]([N:25]1[CH2:26][CH2:27][C:22]([N:15]([C:12](=[O:11])[CH2:13][CH3:14])[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:23][CH2:24]1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 941851-Phenyl-2-propanolHCID 12298181HCID 12298181, compound

Product 1

HCID 12298063HCID 12298063, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 3.54 parts of α-methylphenethyl alcohol, methanesulfonate ester, 4.6 parts of ethyl 4-[N-(1-oxopropyl)-N-phenylamino]-4-piperidinecarboxylate, 3.97 parts of sodium carbonate and 160 parts of 4-methyl-2-pentanone is stirred and refluxed for 16 hours. The reaction mixture is cooled and filtered. The filtrate is washed twice with 200 parts of water, dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 5% of methanol as eluent. The first fraction is collected and the eluent is evaporated. The residue is converted into the ethanedioate salt in 2-propanol. The whole is evaporated and the residual salt is crystallized from 80 parts of 4-methyl-2-pentanone. The product is filtered off and dried in vacuo at 120° C, yielding ethyl 1-(1-methyl-2-phenylethyl)-4[N-(1-oxopropyl)-N-phenylamino]-4-piperidinecarboxylate ethanedioate; m.p. 201.8° C.

Workup

  1. temperaturerefluxed for 16 hours
  2. temperatureThe reaction mixture is cooled
  3. filtrationfiltered
  4. washThe filtrate is washed twice with 200 parts of water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is purified by column-chromatography over silica gel using
  9. additiona mixture of trichloromethane and 5% of methanol as eluent
  10. customThe first fraction is collected
  11. customthe eluent is evaporated
  12. customThe whole is evaporated
  13. customthe residual salt is crystallized from 80 parts of 4-methyl-2-pentanone
  14. filtrationThe product is filtered off
  15. customdried in vacuo at 120° C

Sources & evidence

ORD record
ord-2d5322b90ecf4e028b40bca422b132f8
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

Loading…