HCID 68125536, compound → HCID 68126335, compound

HRID 1283983Notes

Reaction equation

HRID 1283983 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([C:14](O)=[O:15])[C@@H:9]1[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][Li]>C(OCC)C>[C:14]([C@H:10]1[CH2:11][CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C@H:9]1[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)(=[O:15])[CH3:26]

Participants

4

Reactant 2

HCID 68125536HCID 68125536, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 68126335HCID 68126335, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 33.9 g. of cis-1-benzyl-2-(p-methoxybenzyl)-3-piperidinecarboxylic acid in 340 ml. of diethyl ether is stirred at room temperature while 200 ml. of 1M methyl lithium is added dropwise. After this addition is completed, the reaction mixture is stirred and refluxed for 4 hours and poured over ice. The ether layer is separated and washed with 100 ml. of saturated aqueous sodium bicarbonate solution, dried, and filtered. The filtrate is concentrated to yield cis-3-acetyl-1-benzyl-2-(p-methoxybenzyl)piperidine.

Workup

  1. additionAfter this addition
  2. temperaturerefluxed for 4 hours
  3. additionpoured over ice
  4. customThe ether layer is separated
  5. washwashed with 100 ml
  6. dry with materialof saturated aqueous sodium bicarbonate solution, dried
  7. filtrationfiltered
  8. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-ee43e29f74fa444cade4c2ef9f63926f
Source dataset
uspto-grants-1976_08
Patent number
US03976653

Reaction notes

Loading…