Trifluoroacetic acid → N,N-Dimethyl-3-piperidinecarboxamide

HRID 432831

Reaction equation

HRID 432831 reaction equation
N1CCCC(CC(OCC)=O)C1.[CH3:13][N:14]([CH3:23])[C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[N:18][CH:17]=1.FC(F)(F)C(O)=O>[Pt]=O>[CH3:13][N:14]([CH3:23])[C:15]([CH:16]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]1)=[O:22]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 81444N,N-DimethylnicotinamideHCID 2760464Ethyl 2-(piperidin-3-yl)acetate

Product 1

HCID 18760276N,N-Dimethyl-3-piperidinecarboxamideYield 38.4%

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

This reaction was run in the same manner as ethyl 3-piperidinylacetate, starting with commercially available N,N-dimethylnicotinamide (10 g; 66.7 mmol) and platinum oxide (1.02 g; 4.49 mmol). Trifluoroacetic acid (5.1 ml; 66.2 mmol) was used in place of L(+) tartaric acid. Crude product was purified by distillation at approximately 150° C./10 torr, giving N,N-dimethyl-3-piperidinecarboxamide (4.0 g) as a colorless oil. MS m/z (positive ion) 157 (MH+: 100).

Workup

  1. distillationCrude product was purified by distillation at approximately 150° C./10 torr

Sources & evidence

ORD record
ord-18054757282c498b95f60d33afcae9e4
Source dataset
uspto-grants-2003_12
Patent number
US06664271B1

Linked notes

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