2-(cis-2,6-Dimethyl-1-piperidinyl)ethanamine → (R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)propionamide

HRID 1906285Notes

Reaction equation

HRID 1906285 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([CH:7]([CH3:13])[C:8]([O:10]CC)=O)[C:3]1=[O:14].[CH3:15][C@H:16]1[CH2:21][CH2:20][CH2:19][C@@H:18]([CH3:22])[N:17]1[CH2:23][CH2:24][NH2:25]>>[CH3:15][C@H:16]1[CH2:21][CH2:20][CH2:19][C@@H:18]([CH3:22])[N:17]1[CH2:23][CH2:24][NH:25][C:8](=[O:10])[CH:7]([N:4]1[CH2:5][CH2:6][CH:2]([OH:1])[C:3]1=[O:14])[CH3:13]

Participants

3

Reactant 2

HCID 7837022-(cis-2,6-Dimethyl-1-piperidinyl)ethanamineHCID 76485496ethyl (R/S)-2-(3-hydroxy-2-oxo-1-pyrroldinyl)propionate

Product 1

HCID 54290896(R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)propionamide

Procedure

1.5 g of ethyl (R/S)-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)propionate are left to stand at room temperature for 24 hours with 2.45 g of cis-2-(2,6-dimethyl-1-piperidinyl)ethylamine. Thereafter, the excess cis-2-(2,6-dimethyl-1-piperidinyl)ethylamine is distilled off in a high vacuum and the residue (3.5 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)propionamide which is eluted with methanol has a melting point of 129°-130° after recrystallization from ethyl acetate.

Workup

  1. distillationThereafter, the excess cis-2-(2,6-dimethyl-1-piperidinyl)ethylamine is distilled off in a high vacuum
  2. customthe residue (3.5 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)propionamide which is eluted with methanol
  4. customafter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-801ce0d750b94ee8b5b3297796ccbaa7
Source dataset
uspto-grants-1987_03
Patent number
US04650878

Reaction notes

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