2-Bromopropane → 1-Isopropylpyridinium-4-carboxamide bromide

HRID 397550

Reaction equation

HRID 397550 reaction equation
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[Br:10][CH:11]([CH3:13])[CH3:12]>CN(C=O)C>[Br-:10].[CH:11]([N+:5]1[CH:6]=[CH:7][C:2]([C:1]([NH2:9])=[O:8])=[CH:3][CH:4]=1)([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 63582-BromopropaneHCID 15074Isonicotinamide

Product 1

HCID 234977611-Isopropylpyridinium-4-carboxamide bromideYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 200 mL of DMF, containing 50.0 g of isonicotinamide and 60 mL of 2-bromopropane, was refluxed 5.75 h. A white insoluble solid filtered from this cool solution gave 64.9 g (65%) of 1-isopropylpyridinium-4-carboxamide bromide, m/e=165, NMR. Catalytic reduction of this salt, with PtO2 in MeOH, gave 65.2 g (98%) of 1-isopropylpiperidine-4-carboxamide hydrobromide, m/e=171. An aqueous solution of this salt was basified, evaporated to dryness, and extracted with EtOAc to give 39.7 g (90%) of 1-isopropylpiperidine-4-carboxamide free base.

Workup

  1. temperaturewas refluxed 5.75 h
  2. filtrationA white insoluble solid filtered from this cool solution

Sources & evidence

ORD record
ord-2b9dddca4f9940ed9ffd353189dd5876
Source dataset
uspto-grants-2003_08
Patent number
US06610704B1

Linked notes

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