Benzoyl chloride → 3,6-dihydro-2H-pyridin-1-yl(phenyl)methanone

HRID 244272Notes

Reaction equation

HRID 244272 reaction equation
[NH:1]1[CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl>[N:1]1([C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:21])[CH2:2][CH2:3][CH:4]=[CH:5][CH2:6]1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 127501,2,3,6-Tetrahydropyridine

Product 1

HCID 5700373,6-dihydro-2H-pyridin-1-yl(phenyl)methanoneYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a solution of 1,2,3,6-tetrahydropyridine (1.00 g, 12.0 mmol) and triethylamine (3 mL) in CH2Cl2 (30 mL), benzoyl chloride (1.69 g, 12.0 mmol) was added dropwise at 0° C. The reaction mixture was stirred at room temperature for 2 hrs and washed with saturated Na2CO3 (20 mL×3) and brine solution (20 mL), dried over Na2SO4 and concentrated under vacuum to afford crude product. The crude product was purified by silica gel column chromatography using hexane/ethyl acetate (10/3, v/v) to afford target product as a colorless oil (2.27 g, 100%). 1H NMR (CDCl3): δ 2.16-2.25 (m, 2H), 3.46-4.20 (m, 4H), 5.53-5.91 (m, 2H), 7.29-7.53 (m, 5H).

Workup

  1. washwashed with saturated Na2CO3 (20 mL×3) and brine solution (20 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customto afford crude product
  5. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-97d67a3742724e069ea3b1124c83fa53
Source dataset
uspto-grants-2014_02
Patent number
US08658131B2

Reaction notes

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