3-Methylpyridine-2-carboxamide → Rac-cis-3-methylpiperidine-2-carboxamide

HRID 60790Notes

Reaction equation

HRID 60790 reaction equation
[CH3:1][C:2]1[C:3]([C:8]([NH2:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1>C(O)(=O)C.O=[Pt]=O>[CH3:1][C@H:2]1[CH2:7][CH2:6][CH2:5][NH:4][C@H:3]1[C:8]([NH2:10])=[O:9]

Participants

4

Reactant 1

HCID 166410233-Methylpyridine-2-carboxamide

Product 1

HCID 94402189Rac-cis-3-methylpiperidine-2-carboxamideYield 86%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 3-methylpicolinamide (2.23 g, 16.4 mmol) and PtO2 (0.18 g, 0.8 mmol) in acetic acid (55 mL) was placed in a Parr shaker type hydrogenation apparatus, pressurized to 4.70 bar with H2 and maintained at rt for 7 h. The mixture was filtered through diatomaceous earth and the filtrate was concentrated in vacuo to a solid. A mixture of this crude solid and DCM and solid Na2CO3, were stirred at rt overnight. The resulting suspension was filtered and the filtrate was concentrated in vacuo to provide rac-cis-3-methylpiperidine-2-carboxamide as a white solid (2.0 g, 86% yield). 1H NMR (CDCl3, 400 MHz) δ 6.51 (brs, 1H), 5.32 (brs, 1H), 3.37 (d, 1H), 3.14-3.10 (m, 1H), 2.70-2.63 (m, 1H), 2.33-2.28 (m, 1H), 1.73-1.58 (m, 4H), 1.42-1.39 (m, 1H), 1.00 (d, 3H).

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. concentrationthe filtrate was concentrated in vacuo to a solid
  3. additionA mixture of this crude solid and DCM and solid Na2CO3
  4. filtrationThe resulting suspension was filtered
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-857c7b78a03b40379aca29acd9e51f84
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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