Acetyl chloride → 4-{3-[4-(Methylthio)benzyl]-1,2,4-oxadiazol-5-yl}piperidine hydrochloride

HRID 1593004Notes

Reaction equation

C([Cl:4])(=O)C.[CH3:5][S:6][C:7]1[CH:31]=[CH:30][C:10]([CH2:11][C:12]2[N:16]=[C:15]([CH:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]3)[O:14][N:13]=2)=[CH:9][CH:8]=1>CO>[ClH:4].[CH3:5][S:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:11][C:12]2[N:16]=[C:15]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[O:14][N:13]=2)=[CH:30][CH:31]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Acetyl chloride (86 μL, 1.21 mmol) was added dropwise to methanol (0.5 mL) and stirred for 10 minutes then added to tert-butyl 4-{3-[4-(methylthio)benzyl]-1,2,4-oxadiazol-5-yl}piperidine-1-carboxylate (237 mg, 0.61 mmol) in MeOH (5 mL) and the mixture heated to 60° C. for 1 hour and the solvents evaporated to give a the title compound as a yellow powder, (199 mg, 100%); MS: 290 (MH+).

Workup

customthe solvents evaporated

Sources & evidence

ORD record: ord-360ff4f085184d7db5c58602999b9d03
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07294636B2

Reaction notes

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