Potassium Hydroxide → 3-Pyrrolidinecarboxamide, 2,2,5,5-tetramethyl-

HRID 1656882Notes

Reaction equation

HRID 1656882 reaction equation
Br.Br[CH:3]1[C:8](=[O:9])[CH:7](Br)[C:6]([CH3:12])([CH3:11])[NH:5][C:4]1([CH3:14])[CH3:13].[OH-].[K+].[OH-].[NH4+:18]>>[C:8]([CH:7]1[CH2:14][C:4]([CH3:3])([CH3:13])[NH:5][C:6]1([CH3:11])[CH3:12])(=[O:9])[NH2:18]

Participants

4

Reactant 3

HCID 14797Potassium HydroxideHCID 14923Ammonium HydroxideHCID 892514-Piperidinone, 3,5-dibromo-2,2,6,6-tetramethyl-, hydrobromide (1:1)

Product 1

HCID 697083-Pyrrolidinecarboxamide, 2,2,5,5-tetramethyl-

Procedure

3,5-Dibromo-4-oxo-2,2,6,6-tetramethylpiperidine (II, 30 gm) was added slowly, with stirring, to ammonium hydroxide (500 mL). When the solid is dissolved, potassium hydroxide is added, which results in the precipitation of (III). After filtering the solid, additional potassium hydroxide is added to the remaining solution until the precipitation of more material no longer is observed. The precipitates are combined, dried and recrystallized from benzene, giving a white solid (III, 10 gm, 68%) mp 176°-178° C. (lit ref. [1, except pg. 204] mp 180°-181° C). Both I.R. and NMR confirm the structure of (III).

Workup

  1. dissolutionWhen the solid is dissolved

Sources & evidence

ORD record
ord-bb5609b0ab9a48de92ad690d4438e896
Source dataset
uspto-grants-1993_10
Patent number
US05256397

Reaction notes

Loading…