2-Methylpiperidine → 5-Methyl-6-(2-methylpiperidin-1-yl)nicotinonitrile

HRID 400737Notes

Reaction equation

HRID 400737 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH3:10])[C:6](F)=[N:7][CH:8]=1)#[N:2].[CH3:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][NH:13]1>>[CH3:10][C:5]1[C:6]([N:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH:12]2[CH3:11])=[N:7][CH:8]=[C:3]([CH:4]=1)[C:1]#[N:2]

Participants

3

Reactant 2

HCID 79742-MethylpiperidineHCID 232882695-Cyano-2-fluoro-3-picoline

Product 1

HCID 674005855-Methyl-6-(2-methylpiperidin-1-yl)nicotinonitrileYield 93%

Procedure

A solution of 5-cyano-2-fluoro-3-methylpyridine (Molekula, 1.50 g; 11.02 mmol) and 2-methylpiperidine (5.20 mL; 44.08 mmol) was heated to 90° C. for 18 h. Reaction mixture was extracted with EtOAc, the organics dried over MgSO4, evaporated under vacuum to give the title compound as a brown oil (2.2 g, 93%). 1H NMR (DMSO-d6) δ 8.46 (d, J=2.3 Hz, 1H), 7.82 (d, J=2.3 Hz, 1H), 4.01-3.96 (m, 1H), 3.37-3.25 (m, 2H), 3.17-3.09 (m, 1H), 2.22 (s, 3H), 1.72-1.46 (m, 6H), 1.11 (d, J=6.6 Hz, 3H). HPLC (Method B) Rt 3.60 min (Purity: 84.5%). LC/MS (Method A): 216.2 (M+H)+.

Workup

  1. customReaction mixture
  2. extractionwas extracted with EtOAc
  3. dry with materialthe organics dried over MgSO4
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-844f34e963f0429ebd9ec25bad0965e2
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

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