Chloroacetonitrile → HCID 59729268, compound

HRID 600471Notes

Reaction equation

HRID 600471 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4](=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[C:8]#[N:9])[CH2:3][CH2:2]1.[CH3:16][CH2:17][N:18](CC)CC.ClCC#N>C1COCC1>[C:17]([CH2:16][N:1]1[CH2:6][CH2:5][C:4](=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[C:8]#[N:9])[CH2:3][CH2:2]1)#[N:18]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 8471TriethylamineHCID 59347398HCID 59347398, compound

Product 1

HCID 59729268HCID 59729268, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(piperidin-4-ylidene)-2-(pyridin-2-yl)acetonitrile (560 mg, 2.8 mmol) in THF (20 mL) was added NEt3 (5 mL, 38 mmol) and chloroacetonitrile (3 mL, 47 mmol) and the reaction was stirred 16 h. The resulting precipitates were filtered away and the filtrate concentrated to dryness. The residues was purified by silica gel chromatography (Biotage 40-short, 50% EtOAc/hexanes to 100% EtOAc/hexanes) to yield 52 (470 mg, 2.0 mmol, 71%) as a yellow solid. 1H NMR: (500 MHz, CDCl3) δ 8.64 (br d, J=4.9 Hz, 1H), 7.77 (ddd, J=7.9, 7.6, 1.9 Hz, 1H), 7.50 (d, J=7.9 Hz, 1H), 7.27 (dd, J=7.6, 4.9 Hz, 1H), 3.58 (s, 2H), 2.94 (t, J=5.8 Hz, 2H), 2.91 (t, J=5.8 Hz, 2H), 2.83 (t, J=5.8 Hz, 2H), 2.67 (t, J=5.8 Hz, 2H); LC/MS: (ES+) m/z (M+H)+=239; HPLC Rt=0.99 min., column 0, conditions B.

Workup

  1. customThe resulting precipitates
  2. filtrationwere filtered away
  3. concentrationthe filtrate concentrated to dryness
  4. customThe residues was purified by silica gel chromatography (Biotage 40-short, 50% EtOAc/hexanes to 100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-041a05e531e64575b6e33a7b7e1d986a
Source dataset
uspto-grants-2011_03
Patent number
US07902204B2

Reaction notes

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