Chloroacetonitrile → 2-(4-oxopiperidin-1-yl)acetonitrile

HRID 1058610Notes

Reaction equation

HRID 1058610 reaction equation
O.Cl.[NH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.Cl[CH2:11][C:12]#[N:13].C(N(C(C)C)CC)(C)C>O1CCCC1>[O:9]=[C:6]1[CH2:7][CH2:8][N:3]([CH2:11][C:12]#[N:13])[CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 81531DiisopropylethylamineHCID 2723901Piperonylamine

Product 1

HCID 27609212-(4-oxopiperidin-1-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 25.0 g of 4-piperidinone monohydrochloride monohydrate, 11.5 ml of chloroacetonitrile and 57.0 ml of diisopropylethylamine in 250 ml of tetrahydrofuran was refluxed for 10 hours. After the reaction, an insoluble matter was filtered off. The filtrate was added with saturated aqueous sodium hydrogencarbonate solution and extracted with a mixture of ethyl acetate and methanol (10:1). The extract was dried, and the solvent was evaporated to give brown crystals. The crystals were washed with a mixture of ethyl acetate and n-heptane to give 15.7 g of pale brown crystals.

Workup

  1. temperaturewas refluxed for 10 hours
  2. customAfter the reaction
  3. filtrationan insoluble matter was filtered off
  4. additionThe filtrate was added with saturated aqueous sodium hydrogencarbonate solution
  5. extractionextracted with a mixture of ethyl acetate and methanol (10:1)
  6. customThe extract was dried
  7. customthe solvent was evaporated
  8. customto give brown crystals
  9. washThe crystals were washed with a mixture of ethyl acetate and n-heptane

Sources & evidence

ORD record
ord-d96a4e9b8c024403a4170b9d176b4a83
Source dataset
uspto-grants-2003_02
Patent number
US06518265B1

Reaction notes

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