Potassium Carbonate → 4-(3,4-Dichlorophenoxy)-1-(2-oxiran-2-ylethyl)piperidine

HRID 2233370Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 4-(3,4-dichlorophenoxy)piperidine (WO 0058305, WO 0177101) (2.00 g), 2-(2-bromoethyl)oxirane (J. Am. Chem. Soc. 1981, 103, 7520-8) (1.36 g) and potassium carbonate (2.2 g) in acetone (20 ml) was stirred at 50° C. for 12 h. The solvent was removed under vacuum. The residue was partitioned between water and ethyl acetate. The organic layer was washed with water, brine and dried over magnesium sulfate. The mixture was filtered and the solvent was evaporated to afford the subtitle compound as a yellow oil (2.50 g) which was used without further purification in the next step.

Workup

customThe solvent was removed under vacuum
customThe residue was partitioned between water and ethyl acetate
washThe organic layer was washed with water, brine
dry with materialdried over magnesium sulfate
filtrationThe mixture was filtered
customthe solvent was evaporated

Sources & evidence

ORD record: ord-3d1e2a1007714e32914431f9fd74a07c
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709500B2

Reaction notes

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