Potassium Iodide → N-(4-(Methoxymethyl)-1-(2-phenylethyl)-4-piperidinyl)-N-phenylpropanamide

HRID 1973823Notes

Reaction equation

HRID 1973823 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:10][O:11][CH2:12][C:13]1([N:19]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:20](=[O:23])[CH2:21][CH3:22])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.[I-].[K+].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)CC(=O)C>[CH3:10][O:11][CH2:12][C:13]1([N:19]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:20](=[O:23])[CH2:21][CH3:22])[CH2:18][CH2:17][N:16]([CH2:2][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7666Phenethyl bromideHCID 10340Sodium CarbonateHCID 162172Noralfentanil

Product 1

HCID 124716N-(4-(Methoxymethyl)-1-(2-phenylethyl)-4-piperidinyl)-N-phenylpropanamide

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 3.1 parts of 2-bromoethylbenzene, 4.1 parts of N-[4-(methoxymethyl)-4-piperidinyl]-N-phenylpropanamide, 0.1 parts of potassium iodide, 2.4 parts of sodium carbonate and 80 parts of 4-methyl-2-pentanone is stirred and refluxed for 48 hours. The reaction mixture is poured onto water and the whole is shaken thoroughly. 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 5% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The oily residue solidifies on triturating in n-hexane. The product is filtered off and dried, yielding N-[4-(methoxymethyl)-1-(2-phenylethyl)-4-piperidinyl]-N-phenylpropanamide; mp. 85° C.

Workup

  1. temperaturerefluxed for 48 hours
  2. additionThe reaction mixture is poured onto water
  3. stirringthe whole is shaken thoroughly
  4. customThe organic phase is separated
  5. washwashed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe oily residue is purified by column-chromatography over silica gel using
  10. additiona mixture of trichloromethane and 5% of methanol as eluent
  11. customThe pure fractions are collected
  12. customthe eluent is evaporated
  13. customon triturating in n-hexane
  14. filtrationThe product is filtered off
  15. customdried

Sources & evidence

ORD record
ord-64030a7bccb94acbb57959bbad21c2e5
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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