trans-3-[2,6-Dimethylpiperidinyl]propylamine → N-[3-[2,6-dimethyl-1-piperidinyl]propyl]-hexahydro-5-oxo-1H-pyrrolizine-3-carboxamide

HRID 980453Notes

Reaction equation

HRID 980453 reaction equation
C(O[C:4]([CH:6]1[N:13]2[CH:9]([CH2:10][CH2:11][C:12]2=[O:14])[CH2:8][CH2:7]1)=[O:5])C.[CH3:15][C@H:16]1[CH2:21][CH2:20][CH2:19][C@H:18]([CH3:22])[N:17]1[CH2:23][CH2:24][CH2:25][NH2:26]>>[CH3:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH:18]([CH3:22])[N:17]1[CH2:23][CH2:24][CH2:25][NH:26][C:4]([CH:6]1[N:13]2[CH:9]([CH2:10][CH2:11][C:12]2=[O:14])[CH2:8][CH2:7]1)=[O:5]

Participants

3

Reactant 2

HCID 7176134trans-3-[2,6-Dimethylpiperidinyl]propylamineHCID 13756031hexahydro-5-oxo-1H-pyrrolizine-3-carboxylic acid ethyl ester

Product 1

HCID 20221664N-[3-[2,6-dimethyl-1-piperidinyl]propyl]-hexahydro-5-oxo-1H-pyrrolizine-3-carboxamide

Procedure

A solution of hexahydro-5-oxo-1H-pyrrolizine-3-carboxylic acid ethyl ester (5.0 g, 0.0254 mol) in trans-3-[2,6-dimethylpiperidinyl]propylamine (34 g, 0.2 mol) is stirred at room temperature 24 hours. The solution is concentrated at reduced pressure and distilled to yield N-[3-[2,6-dimethyl-1-piperidinyl]propyl]-hexahydro-5-oxo-1H-pyrrolizine-3-carboxamide, trans-isomer.

Workup

  1. concentrationThe solution is concentrated at reduced pressure
  2. distillationdistilled

Sources & evidence

ORD record
ord-1867061964c643f582d391d65a673c37
Source dataset
uspto-grants-1987_01
Patent number
US04638006

Reaction notes

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