2-(cis-2,6-Dimethyl-1-piperidinyl)ethanamine → cis-(+-)-N-(2-(2,6-Dimethyl-1-piperidinyl)ethyl)-2-oxo-3-hydroxy-1-pyrrolidineacetamide

HRID 1906267Notes

Reaction equation

HRID 1906267 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]([O:10]CC)=O)[C:3]1=[O:13].[CH3:14][C@H:15]1[CH2:20][CH2:19][CH2:18][C@@H:17]([CH3:21])[N:16]1[CH2:22][CH2:23][NH2:24]>C(OCC)C>[CH3:14][C@H:15]1[CH2:20][CH2:19][CH2:18][C@@H:17]([CH3:21])[N:16]1[CH2:22][CH2:23][NH:24][C:8](=[O:10])[CH2:7][N:4]1[CH2:5][CH2:6][CH:2]([OH:1])[C:3]1=[O:13]

Participants

4

Reactant 2

HCID 7837022-(cis-2,6-Dimethyl-1-piperidinyl)ethanamineHCID 13385945ethyl (R/S)-2-(3-hydroxy-2oxo-1-pyrrolidinyl)acetate

Product 1

HCID 3069833cis-(+-)-N-(2-(2,6-Dimethyl-1-piperidinyl)ethyl)-2-oxo-3-hydroxy-1-pyrrolidineacetamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4.5 g of ethyl (R/S)-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetate are heated to 100° for 3.5 hours under nitrogen with 7.1 g of cis-2-(2,6-dimethyl-1-piperidinyl)ethylamine. Thereafter, diethyl ether is added thereto, the mixture is stirred, filtered and the filter residue (6.5 g) is chromatographed on 30 g of silica gel (granular size 0.2--0.5 mm). The (R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetamide which is eluted with methylene chloride and methanol has a melting point of 131°-132° after recrystallization from ethyl acetate.

Workup

  1. filtrationfiltered
  2. customthe filter residue (6.5 g) is chromatographed on 30 g of silica gel (granular size 0.2--0.5 mm)
  3. washThe (R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetamide which is eluted with methylene chloride and methanol
  4. customafter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-6df267ed8bf24496a861cae6bc74d79c
Source dataset
uspto-grants-1987_03
Patent number
US04650878

Reaction notes

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