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

HRID 1448321Notes

Reaction equation

HRID 1448321 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 silicagel 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. 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 silicagel
  9. additiona mixture of trichloromethane and 5% of methanol as eluent
  10. customThe pure fractions are collected
  11. customthe eluent is evaporated
  12. customon triturating in n-hexane
  13. filtrationThe product is filtered off
  14. customdried

Sources & evidence

ORD record
ord-12e115ec7f5443398e7ae2f28491482d
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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