Sodium Iodide → HCID 23324836, compound

HRID 1380961Notes

Reaction equation

HRID 1380961 reaction equation
[CH3:1][O:2][CH2:3][C:4]1([N:10]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11](=[O:13])[CH3:12])[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].Cl[CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(C(C)=O)C(C)C>[C:33]1([CH2:32][CH2:31][N:7]2[CH2:8][CH2:9][C:4]([CH2:3][O:2][CH3:1])([N:10]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:11](=[O:13])[CH3:12])[CH2:5][CH2:6]2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 2314961-Chloro-2-phenylethaneHCID 23324747HCID 23324747, compound

Product 1

HCID 23324836HCID 23324836, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 0.67 g of 4-methoxymethyl-4-(N-phenylmethoxyacetamido)piperidine, 0.1 g of sodium iodide, 2.4 g of sodium carbonate, 3.9 g of (2-chloroethyl)benzene and 75 ml of methyl isobutyl ketone is heated to and maintained at a reflux for four days. The reaction mixture is cooled and filtered. The filtrate is evaporated and the resulting oil is purified using a Waters Associates Prep LC/System 500 and a PrepPAK-500/SILICA column. The mobile phase is 5% methanol in ethyl acetate. The eluent is flash evaporated to give 0.42 g of 1-(2-phenylethyl)-4-methoxymethyl-4-(N-phenylmethoxyacetamido)piperidine.

Workup

  1. temperatureis heated to and
  2. temperaturemaintained at
  3. temperaturea reflux for four days
  4. temperatureThe reaction mixture is cooled
  5. filtrationfiltered
  6. customThe filtrate is evaporated
  7. customthe resulting oil is purified
  8. customevaporated

Sources & evidence

ORD record
ord-740c39da574f452499a250b68072c9bf
Source dataset
uspto-grants-1986_04
Patent number
US04584303

Reaction notes

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