Chloroacetonitrile → HCID 86052719, compound

HRID 600466Notes

Reaction equation

HRID 600466 reaction equation
[C:1]1([C:7](=[C:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16][CH2:17][N:18](CC)CC.ClCC#N>C1COCC1>[C:17]([CH2:16][N:13]1[CH2:14][CH2:15][C:10](=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]#[N:9])[CH2:11][CH2:12]1)#[N:18]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 8471TriethylamineHCID 59681564Phenyl(piperidin-4-ylidene)acetonitrile

Product 1

HCID 86052719HCID 86052719, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-phenyl-2-(piperidin-4-ylidene)acetonitrile (6.8 g, 34 mmol) in THF (150 mL) was added NEt3 (40 mL, 300 mmol) and chloroacetonitrile (20 mL, 315 mmol) and the reaction was stirred 16 h. The precipitates was filtered away and the filtrate concentrated to dryness. The residues was purified by silica gel chromatography (Biotage 40-short, 20% EtOAc/Hex to 50% EtOAc/Hex) to yield 42 (1.7 g, 7.2 mmol, 21%) as a yellow waxy solid. 1H NMR: (500 MHz, CDCl3) δ 7.44-7.34 (m, 3H), 7.30-7.27 (m, 2H), 3.65 (s, 2H), 2.96 (t, J=5.3 Hz, 2H), 2.90 (t, J=5.3 Hz, 2H), 2.70 (t, J=5.6 Hz, 2H), 2.62 (t, J=5.6 Hz, 2H); LC/MS: (ES+) m/z (M+H)+=238; HPLC Rt=1.33 min., column 0, conditions B.

Workup

  1. filtrationThe precipitates was filtered away
  2. concentrationthe filtrate concentrated to dryness
  3. customThe residues was purified by silica gel chromatography (Biotage 40-short, 20% EtOAc/Hex to 50% EtOAc/Hex)

Sources & evidence

ORD record
ord-d9d9ca67164b46ceb59441fb69d9f12d
Source dataset
uspto-grants-2011_03
Patent number
US07902204B2

Reaction notes

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