Dimethyl Sulfoxide → HCID 22617036, compound

HRID 843266Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][N:12]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)[CH:14]([CH2:26][OH:27])[CH2:13]1.O>C(Cl)Cl>[CH3:11][N:12]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)[CH:14]([CH:26]=[O:27])[CH2:13]1

Participants

Conditions

Temperature: -40 °C

Procedure

To a solution of oxalyl chloride (3.3 mL, 37.9 mmol) in methylene chloride (100 mL) cooled below −40° C. was added dimethyl sulfoxide (5.6 mL, 79 mmol) in methylene chloride (5 mL). The reaction was stirred for another 30 min at −40° C. and 1-methyl-3-hydroxymethyl-4-(3,4-dichlorophenyl)piperidine (9.0 g, 33 mmol) in methylene chloride (100 mL) was added over 15 min while keeping the temperature below −40° C. The reaction was stirred for another 30 min at this temperature and then allowed to heat to room temperature. Water (100 mL) was added and the organic phase separated off. The aqueous phase was extracted with methylene chloride (2×100 mL). The combined organic extracts were dried over magnesium sulphate and evaporated to dryness to give 10 g of the title compound.

Workup

customthe temperature below −40° C
stirringThe reaction was stirred for another 30 min at this temperature
temperatureto heat to room temperature
customthe organic phase separated off
extractionThe aqueous phase was extracted with methylene chloride (2×100 mL)
dry with materialThe combined organic extracts were dried over magnesium sulphate
customevaporated to dryness

Sources & evidence

ORD record: ord-2e261140127c4ce491582d9179832ccc
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06376673B1

Reaction notes

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