(Diethylamino)sulfur trifluoride → HCID 22993538, compound

HRID 1167719Notes

Reaction equation

[C:1]([C:3]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:8][CH2:7][N:6]([C:9]2[C:19]([CH2:20][CH:21](O)[CH3:22])=[CH:18][CH:17]=[C:11]3[C:12]([NH:14][C:15](=[O:16])[C:10]=23)=[O:13])[CH2:5][CH2:4]1)#[N:2].C(N(S(F)(F)[F:36])CC)C>C1C=CC=CC=1>[C:1]([C:3]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:8][CH2:7][N:6]([C:9]2[C:19]([CH2:20][CH:21]([F:36])[CH3:22])=[CH:18][CH:17]=[C:11]3[C:12]([NH:14][C:15](=[O:16])[C:10]=23)=[O:13])[CH2:5][CH2:4]1)#[N:2]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 3-(4-cyano-4-phenylpiperidin-1-yl)-(2-hydroxypropyl)phthalimide (2.60 g, 6.1 mmol) and diethylaminosulfur trifluoride (DAST, 1.96 g, 12.2 mmol) in benzene (100 mL) was stirred and heated at 70° C. under argon atmosphere for 24 h. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using chloroform-methanol-2M ammonia in methanol (1000/28/14) as the eluent, to obtain the desired product as a viscous oil (1.30 g, 50%).

Workup

customThe solvent was evaporated under reduced pressure
customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-ee3056494eb0458f865dfb7d30b54cf5
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06620815B1

Reaction notes

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