Allyl bromide → Methyl-1-[(2-chlorophenyl)methyl]-4-oxo-3-(2-propenyl)-3-piperidine carboxylate

HRID 1089303Notes

Reaction equation

[CH3:1][O:2][C:3]([CH:5]1[C:10](=[O:11])[CH2:9][CH2:8][N:7]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[CH2:6]1)=[O:4].[CH3:20][C:21]([O-])(C)[CH3:22].[K+].C(Br)C=C>C(O)(C)(C)C>[CH3:1][O:2][C:3]([C:5]1([CH2:22][CH:21]=[CH2:20])[C:10](=[O:11])[CH2:9][CH2:8][N:7]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[CH2:6]1)=[O:4]

Participants

Conditions

Temperature: 30 °C

Procedure

14.60 g (51.8 mmol) of methyl-1-[(2-chlorophenyl)methyl]-4-oxo-3-piperidine carboxylate was dissolved in 40 ml of tert-butanol and warmed to 30° C. Within 2 minutes 6.57 g (58.4 mmol) of potassium tert-butylate in 45 ml of tert-butanol was added. After 15 minutes of stirring, 25 ml of tert-butanol was added once more. Then 6.34 g (51.4 mmol) of allylbromide was added within 10 minutes and stirred for 2 more hours at 30° to 35° C. The reaction mixture was concentrated by evaporation and 70 ml of water and 70 ml of ether were added to the residue. The organic phase was washed with 50 ml of sodium sulfate solution, dried on magnesium sulfate and concentrated by evaporation. The yield was 40.68 g of methyl-1-[(2-chlorophenyl)methyl]-4-oxo-3-(2-propenyl)-3-piperidine carboxylate, which equals 88.1 percent. Data concerning the compound was:

Workup

stirringstirred for 2 more hours at 30° to 35° C
concentrationThe reaction mixture was concentrated by evaporation and 70 ml of water and 70 ml of ether
additionwere added to the residue
washThe organic phase was washed with 50 ml of sodium sulfate solution
customdried on magnesium sulfate
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-886eb7b65bc845788f5fc7ddf4e5cf60
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04965359

Reaction notes

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