N-(2-Aminoethyl)piperidine → (R/S)-N-[2-(1-piperidinyl)ethyl]-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetamide

HRID 1087074Notes

Reaction equation

HRID 1087074 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].[NH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>>[N:17]1([CH2:16][CH2:15][NH:14][C:8](=[O:10])[CH2:7][N:4]2[CH2:5][CH2:6][CH:2]([OH:1])[C:3]2=[O:13])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

3

Reactant 2

HCID 33944N-(2-Aminoethyl)piperidineHCID 13385945ethyl (R/S)-2-(3-hydroxy-2oxo-1-pyrrolidinyl)acetate

Product 1

HCID 131713897(R/S)-N-[2-(1-piperidinyl)ethyl]-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetamide

Procedure

3.0 g of ethyl (R/S)-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetate and 2.87 g of N-(2-aminoethyl)piperidine are heated to 100° for 4 hours under nitrogen. The excess N-(2-aminoethyl)piperidine is distilled in a high vacuum. The (R/S)-N-[2-(1-piperidinyl)ethyl]-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetamide remaining as the residue has a melting point of 110°-111° after crystallization from ethyl acetate.

Workup

  1. distillationThe excess N-(2-aminoethyl)piperidine is distilled in a high vacuum
  2. customafter crystallization from ethyl acetate

Sources & evidence

ORD record
ord-9b11a3ad50784ac3b03ca220cbcaf91c
Source dataset
uspto-grants-1991_07
Patent number
US05034402

Reaction notes

Loading…