6-Chloro-3-pyridinecarbonitrile → HCID 24751344, compound

HRID 732938Notes

Reaction equation

HRID 732938 reaction equation
[CH3:1][N:2]([CH2:11][CH2:12][CH2:13][CH:14]1[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]1)[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][N:4]=1.Cl[C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24]N=1.CN[CH2:32][CH2:33]CC1CCN(C)CC1>CCO>[CH3:24][C:25]1[C:26]2[N:27]=[C:7]([C:6]3[CH:9]=[CH:10][C:3]([N:2]([CH3:1])[CH2:11][CH2:12][CH2:13][CH:14]4[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]4)=[N:4][CH:5]=3)[NH:8][C:33]=2[CH:32]=[C:29]([CH3:22])[CH:28]=1

Participants

5

Reactant 3

HCID 51520946-Chloro-3-pyridinecarbonitrileHCID 68657044HCID 68657044, compoundHCID 68657539951223-50-0

Product 1

HCID 24751344HCID 24751344, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-{Methyl-[3-(1-methyl-piperidin-4-yl)-propyl]-amino}-nicotinonitrile. A solution of 6-chloro-nicotinonitrile (322 mg, 2.33 mmol) and methyl-[3-(1-methyl-piperidin-4-yl)-propyl]-amine (0.400 g, 2.56 mmol) in EtOH (10 mL) was heated at 100° C. in a sealed tube for 4 h. The mixture was cooled to rt and concentrated to give a crude product which was purified by FCC to give 260 mg (41%) of the title compound as a yellow oil. 1H NMR (CDCl3): 8.40 (d, J=2.3 Hz, 1H), 7.52 (dd, J=9.0, 2.3 Hz, 1H), 6.39 (d, J=9.0 Hz, 1H), 3.56 (t, J=7.6 Hz, 2H), 3.17 (s, 3H), 2.93-2.73 (m, 2H), 2.33 (s, 3H), 1.97-1.77 (m, 4H), 1.33-1.16 (m, 8H), 0.93-0.77 (m, 1H).

Workup

  1. concentrationconcentrated
  2. customto give a crude product which
  3. customwas purified by FCC

Sources & evidence

ORD record
ord-58e6d7fdd37b471b9c209ab050e65eeb
Source dataset
uspto-grants-2009_09
Patent number
US07589087B2

Reaction notes

Loading…