2-Chloro-6-ethylnicotinonitrile → 2-[(Cyclopentylmethyl)(ethyl)amino]-6-ethylpyridine-3-carbonitrile

HRID 906331Notes

Reaction equation

HRID 906331 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[C:4]([CH2:10][CH3:11])[N:3]=1.[CH:12]1([CH2:17][NH:18][CH2:19][CH3:20])[CH2:16][CH2:15][CH2:14][CH2:13]1>>[CH:12]1([CH2:17][N:18]([CH2:19][CH3:20])[C:2]2[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[C:4]([CH2:10][CH3:11])[N:3]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

3

Reactant 2

HCID 219304332-Chloro-6-ethylnicotinonitrileHCID 43163716N-(cyclopentylmethyl)-N-ethylamine2×

Product 1

HCID 673913322-[(Cyclopentylmethyl)(ethyl)amino]-6-ethylpyridine-3-carbonitrileYield 63%

Conditions

Temperature
100 °C

Procedure

2-Chloro-6-ethylpyridine-3-carbonitrile (500 mg, 3.00 mmol) synthesized by the method described in International Patent Publication WO1997/19078 and N-(cyclopentylmethyl)-N-ethylamine (1.50 g, 11.8 mmol) were mixed, and the mixture was stirred at 100° C. for 8 hours in an argon atmosphere. The mixture was further added with N-(cyclopentylmethyl)-N-ethylamine (0.19 g, 1.49 mmol), and stirred at 100° C. for 8 hours, and then the reaction mixture was azeotroped with toluene. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1) to obtain 2-[(cyclopentylmethyl)(ethyl)amino]-6-ethylpyridine-3-carbonitrile (484 mg, 63%) as pale yellow oil.

Workup

  1. additionwere mixed
  2. stirringstirred at 100° C. for 8 hours
  3. customthe reaction mixture was azeotroped with toluene
  4. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1)

Sources & evidence

ORD record
ord-fd30c89d52d04a128fae663ae814086d
Source dataset
uspto-grants-2011_09
Patent number
US08012989B2

Reaction notes

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