Normeperidine → 4-Carbethoxy-1-carboxymethyl-4-phenylpiperidine

HRID 1658944Notes

Reaction equation

HRID 1658944 reaction equation
[C:1]([C:6]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)([O:3][CH2:4][CH3:5])=[O:2].Cl[CH2:19][C:20]([O-:22])=[O:21].[Na+]>>[C:1]([C:6]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:7][CH2:8][N:9]([CH2:19][C:20]([OH:22])=[O:21])[CH2:10][CH2:11]1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

3

Reactant 2

HCID 32414NormeperidineHCID 23665759Sodium chloroacetate

Product 1

HCID 205073564-Carbethoxy-1-carboxymethyl-4-phenylpiperidineYield 58%

Procedure

4-Carbethoxy-4-phenylpiperidine (4.01 g.) was dissolved in 13 ml. absolute alcohol and refluxed together with 2.01 g. sodium chloroacetate. After 7 hours no starting material was present as evidenced by TLC. The precipitated sodium chloride was removed by filtration and washed with 3 ml. ethanol. On cooling of the filtrate white crystals appeared. Filtration and drying gave 2.9 g. (58%) of the title compound. m.p. 148°-150°C. Evaporation of the mother liquor gave a glass which did not crystallize from acetone/hexane.

Workup

  1. customThe precipitated sodium chloride was removed by filtration
  2. washwashed with 3 ml
  3. temperatureOn cooling of the filtrate white crystals
  4. filtrationFiltration
  5. customdrying
  6. customgave 2.9 g

Sources & evidence

ORD record
ord-88e15f6bd07e4b7fb9aeab9691738e96
Source dataset
uspto-grants-1976_06
Patent number
US03966764

Reaction notes

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