Thionyl Chloride → 1-Methoxy-4-(4-methoxybenzylsulfanyl)-piperidine-4-carbonyl chloride

HRID 2035308Notes

Reaction equation

[CH3:1][O:2][N:3]1[CH2:8][CH2:7][C:6]([S:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)([C:9](O)=[O:10])[CH2:5][CH2:4]1.S(Cl)([Cl:24])=O>C1(C)C=CC=CC=1.CN(C)C=O>[CH3:1][O:2][N:3]1[CH2:8][CH2:7][C:6]([S:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)([C:9]([Cl:24])=[O:10])[CH2:5][CH2:4]1

Participants

Conditions

Temperature: 100 °C

Procedure

700 mg 1-Methoxy-4-(4-methoxy-benzylsulfanyl)-piperidine-4-carboxylic acid (from Step 5) was dissolved in 10 ml toluene, 1 drop N,N-dimethylformamide was added, followed by 400 mg thionyl chloride. The mixture was heated to 100° C. for 1 hour, at which time the evolution of gas has ceased. The solvent was evaporated, to yield crude 1-methoxy-4-(4-methoxy-benzylsulfanyl)-piperidine-4-carbonyl chloride.

Workup

customThe solvent was evaporated

Sources & evidence

ORD record: ord-6b07e230cd494fd79e052defdee85325
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08574607B2

Reaction notes

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