Dichloromethane → 1-Benzyl 3-methyl 4-oxopiperidine-1,3-dicarboxylate

HRID 639851Notes

Reaction equation

HRID 639851 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH:3]1[C:8]([O-:10])=[O:9].[CH2:11]([O:18][C:19](Cl)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:22](Cl)Cl>>[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:19]([O:18][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:20])[CH2:4][CH:3]1[C:8]([O:10][CH3:22])=[O:9]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 10387Benzyl chloroformateHCID 179630544-Oxo-3-piperidinecarboxylate

Product 1

HCID 157481361-Benzyl 3-methyl 4-oxopiperidine-1,3-dicarboxylate

Procedure

To a stirred solution of 4-oxo-3-piperidinecarboxylate (5 g) in dry DCM (50 ml), under N2 atmosphere, TEA (9 mL) was added at rt and then, at 0° C., benzylchloroformate (4.2 mL) was added slowly and stirring was continued for 30 minutes at 0° C. and 1 h at RT. The mixture was quenched at 0° C. with HCl 2N. The aqueous phase was extracted with DCM (2 times) and the combined organic layers were washed with saturated NaCl aqueous solution, dried and concentrated in vacuo to give the title compound (7.5 g).

Workup

  1. customThe mixture was quenched at 0° C. with HCl 2N
  2. extractionThe aqueous phase was extracted with DCM (2 times)
  3. washthe combined organic layers were washed with saturated NaCl aqueous solution
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3054fc7d726a43e89e8bd9c0ef608e4f
Source dataset
uspto-grants-2010_04
Patent number
US07691893B2

Reaction notes

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