Acetone → Ethyl 1-(2-chloroethyl)piperidine-4-carboxylate

HRID 1927022Notes

Reaction equation

HRID 1927022 reaction equation
[NH:1]1[CH2:11][CH2:10][CH2:9][CH:3](C(OCC)=O)[CH2:2]1.Br[CH2:13][CH2:14][Cl:15].[C:16]([O-:19])([O-])=[O:17].[K+].[K+].[CH3:22][C:23](C)=O>>[Cl:15][CH2:14][CH2:13][N:1]1[CH2:2][CH2:3][CH:9]([C:16]([O:19][CH2:22][CH3:23])=[O:17])[CH2:10][CH2:11]1

Participants

5

Reactant 4

HCID 180AcetoneHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 98969Ethyl nipecotate

Product 1

HCID 61287119Ethyl 1-(2-chloroethyl)piperidine-4-carboxylateYield 38.6%

Procedure

To a solution of ethyl nipecotate (20.0 mL, 130 mmol) in acetone (180 mL) was added 1-bromo-2-chloroethane (21.6 mL, 260 mmol) followed by anhydrous K2CO3 (27.12 g, 196 mmol). The reaction mixture was stirred for 24 h and then concentrated under vacuum. The resulting residue was treated with H2O (75 mL) and extracted with Et2O. The combined organic layers were dried with MgSO4, filtered, and concentrated under vacuum. Purification of the crude residue by flash chromatography (50% Et2O/50% hexane) on silica gel gave the title compound (10.99 g, 38.6%). EI-MS m/z 220 (M+H+) Rt (1.20 min).

Workup

  1. concentrationconcentrated under vacuum
  2. additionThe resulting residue was treated with H2O (75 mL)
  3. extractionextracted with Et2O
  4. dry with materialThe combined organic layers were dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customPurification of the crude residue by flash chromatography (50% Et2O/50% hexane) on silica gel

Sources & evidence

ORD record
ord-3ee8cf4b2d57479e958a3e8c044917d9
Source dataset
uspto-grants-2012_05
Patent number
US08183257B2

Reaction notes

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