Water → Ethyl 1-(2-methyl-2-sulfanylpropyl)piperidine-4-carboxylate

HRID 1357834Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.[CH3:12][C:13]1([CH3:16])[CH2:15][S:14]1.O>C1C=CC=CC=1>[CH3:12][C:13]([SH:14])([CH3:16])[CH2:15][N:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

Ethyl piperidine-4-carboxylate (3.6 g, 22.9 mmol) was dissolved in benzene (5 mL), and 2,2-dimethylthiirane (5.04 g, 57.3 mmol) was added. The reaction mixture was stirred at 80° C. for 20 hours, poured into water and extracted several times with EtOAc. The combined organic extracts were washed with brine and dried over anhydrous sodium sulfate. The volatiles were evaporated and the residue was dried under vacuum to afford 5.45 g (97%) of the title compound. 1H NMR (300 MHz, CD3OD) δ 4.12 (q, J=7.1 Hz, 2H), 2.92-2.96 (d, J=11.9 Hz, 2H), 2.19-2.40 (m, 6H), 1.61-1.86 (m, 4H), 1.29 (s, 6H), 1.25 (t, J=7.1 Hz, 2H).

Workup

extractionextracted several times with EtOAc
washThe combined organic extracts were washed with brine
dry with materialdried over anhydrous sodium sulfate
customThe volatiles were evaporated
customthe residue was dried under vacuum

Sources & evidence

ORD record: ord-9b274e22964f4308ae2dc2e054c1a43b
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06593347B2

Reaction notes

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