1-Bromo-2-Chloroethane → Ethyl 1-(2-chloroethyl)-3-piperidinecarboxylate

HRID 654521Notes

Reaction equation

HRID 654521 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2]1.Br[CH2:13][CH2:14][Cl:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:15][CH2:14][CH2:13][N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2]1

Participants

5

Reactant 3

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

Product 1

HCID 15076314Ethyl 1-(2-chloroethyl)-3-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of ethyl 3-piperidylcarboxylate (100 g, 0.64 mole) in acetone (600 ml) was treated with 1-bromo-2-chloroethane (54 ml, 0.64 mole) and anhydrous potassium carbonate (138 g, 1.00 mole) and the mixture stirred at room temperature for 24h. The mixture was concentrated in vacuo and the residue treated with water (400 ml) and extracted with ether (2×200 ml). The combined ether extracts were dried (Na2SO4) and concentrated in vacuo to leave a yellow oil, which was purified by chromatography on silica gel eluting with 50% ether/60-80 petrol to give the title compound (D18) as a pale yellow oil (50.0 g, 36%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue treated with water (400 ml)
  3. extractionextracted with ether (2×200 ml)
  4. dry with materialThe combined ether extracts were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto leave a yellow oil, which
  7. customwas purified by chromatography on silica gel eluting with 50% ether/60-80 petrol

Sources & evidence

ORD record
ord-689572b7eae543828d51e6109b7e280d
Source dataset
uspto-grants-1992_07
Patent number
US05132316

Reaction notes

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