Toluene → 1-(2-phenylethyl)-4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine

HRID 1380957Notes

Reaction equation

HRID 1380957 reaction equation
[CH3:1][O:2][C:3]([C:5]1([N:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12](=[O:14])[CH3:13])[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)=[O:4].[I].[Na].C(=O)([O-])[O-].[Na+].[Na+].[CH2:31](C(C)=O)C(C)C.[C:38]1([CH3:44])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>>[C:38]1([CH2:44][CH2:31][N:8]2[CH2:9][CH2:10][C:5]([C:3]([O:2][CH3:1])=[O:4])([N:11]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:12](=[O:14])[CH3:13])[CH2:6][CH2:7]2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 5

HCID 1140TolueneHCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 233248214-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidineHCID 178506594HCID 178506594, compound

Product 1

HCID 233247971-(2-phenylethyl)-4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine

Procedure

A mixture of 1 g of 4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine, 0.12 sodium iodine, 3.5 g of sodium carbonate, 0.47 g of 2-chlroethylbenzene and 50 ml of methyl isobutyl ketone is maintained at reflux for six days. The mixture is cooled, diluted with 500 ml of toluene and washed three times with 20 ml of water. The organic phase is dried over 20 g of sodium sulfate. The solid is filtered off and the solvent flash evaporated to give an oil. The oil is purified using a Waters Associates Prep LC/System 500 and a PrePAK-500/SILICA column (ethyl acetate). A yield of 0.51 g of 1-(2-phenylethyl)-4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine is isolated, combined with 0.06 g of oxalic acid in methanol and heated to reflux. Methyl t-butyl ether is added dropwise to the refluxing solution until a cloud point is reached. Additional methonol is added to the cloudy refluxing solution until it clears. The solution is cooled and the precipitate collected via filtration. The precipitate is dried under vacuo to give 0.46 g of 1-(2-phenylethyl)-4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidinium oxalate, m.p. 170°-172° C. (decomp.).

Workup

  1. temperatureis maintained
  2. temperatureat reflux for six days
  3. temperatureThe mixture is cooled
  4. washwashed three times with 20 ml of water
  5. dry with materialThe organic phase is dried over 20 g of sodium sulfate
  6. filtrationThe solid is filtered off
  7. customthe solvent flash evaporated
  8. customto give an oil
  9. customThe oil is purified

Sources & evidence

ORD record
ord-35adfcd2ec094c69acc4f78587a19089
Source dataset
uspto-grants-1986_04
Patent number
US04584303

Reaction notes

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