Chloroacetyl chloride → 1-(4-Benzylpiperidin-1-yl)-2-chloroethan-1-one

HRID 1267148Notes

Reaction equation

HRID 1267148 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Cl:20][CH2:21][C:22](Cl)=[O:23]>C1COCC1>[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([C:22]([CH2:21][Cl:20])=[O:23])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 317384-Benzylpiperidine

Product 1

HCID 11296081-(4-Benzylpiperidin-1-yl)-2-chloroethan-1-oneYield 91.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-benzylpiperidine (17.5 g, 100 mmol) in THF (250 mL) was treated with K2CO3 (14 g, 101 mmol) and chloroacetylchloride (11.3 g, 100 mmol) at rt for 2 hours. The reaction mixture was filtered. The filtrate was concentrated, and then dissolved in EtOAc and water. The organic layer was washed with brine, dried over MgSO4, and concentrated to give the product (21.6 g, 91.5%). 1H NMR (CDCl3) δ 7.32-7.12 (m, 5H), 4.09 (s, 2H), 3.79-3.76 (m, 2H), 2,56 (d, J=7.0 Hz, 2H), 1.89-1.80 (m, 1H), 1.79-1.71 (m, 4H), 1.28-1.12 (m, 2H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationThe filtrate was concentrated
  3. dissolutiondissolved in EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ad19df94966747f3810b43ff32769052
Source dataset
uspto-grants-2003_04
Patent number
US06552042B2

Reaction notes

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