Ethyl 2-oxopyrrolidine-1-acetate → cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-oxo-1-pyrrolidineacetamide

HRID 614464

Reaction equation

HRID 614464 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]([O:10]CC)=O.[CH3:13][C@H:14]1[CH2:19][CH2:18][CH2:17][C@@H:16]([CH3:20])[N:15]1[CH2:21][CH2:22][NH2:23]>>[CH3:13][C@H:14]1[CH2:19][CH2:18][CH2:17][C@@H:16]([CH3:20])[N:15]1[CH2:21][CH2:22][NH:23][C:8](=[O:10])[CH2:7][N:3]1[CH2:4][CH2:5][CH2:6][C:2]1=[O:1]

Participants

3

Reactant 2

HCID 109094Ethyl 2-oxopyrrolidine-1-acetateHCID 7837022-(cis-2,6-Dimethyl-1-piperidinyl)ethanamine

Product 1

HCID 44374502cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-oxo-1-pyrrolidineacetamide

Procedure

A mixture of 17.1 g. of ethyl 2-oxo-1-pyrrolidineacetate (U.S. Pat. No. 3,459,738) and 25.4 g. of cis-2-(2,6-dimethyl-1-piperidinyl)ethylamine (U.S. Pat. No. 3,446,811) is heated at 95°-100° C. for 16 hours. The excess cis-2-(2,6-dimethyl-1-piperidinyl)ethylamine is evaporated at reduced pressure and the residue is fractionated. The product, cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-oxo-1-pyrrolidineacetamide, is obtained as an oil, b.p. 178°-183° C./0.15 mm., which crystallizes on standing; m.p. 93°-94.5° C. after two crystallizations from ethyl acetate-pentane.

Workup

  1. additionA mixture of 17.1 g
  2. temperature3,446,811) is heated at 95°-100° C. for 16 hours
  3. customThe excess cis-2-(2,6-dimethyl-1-piperidinyl)ethylamine is evaporated at reduced pressure

Sources & evidence

ORD record
ord-815e44c15b814a78b439b7075ca8da80
Source dataset
uspto-grants-1979_03
Patent number
US04145347

Linked notes

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