Triethylamine → HCID 86614580, compound

HRID 1723823Notes

Reaction equation

[F:1][C:2]([F:19])([O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1)[CH:3]([F:5])[F:4].C(N(CC)CC)C.[CH:27]([S:35](Cl)(=[O:37])=[O:36])=[CH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)Cl>[C:29]1([CH:28]=[CH:27][S:35]([N:16]2[CH2:17][CH2:18][N:13]([C:10]3[CH:11]=[CH:12][C:7]([O:6][C:2]([F:1])([F:19])[CH:3]([F:4])[F:5])=[CH:8][CH:9]=3)[CH2:14][CH2:15]2)(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]piperazine (1.39 g, 0.005 mol) was dissolved in DCM (250 ml) and triethylamine (2.1 ml, 0.015 mol) was added. This was cooled to 0° C. and styrene sulphonyl chloride (CAS Number 52147-97-4, 1.11 g, 0.0055 mol) was added. Allowed to reach ambient temperature and stirred overnight. Washed with H2O and separated off the organic phase. Dried over MgSO4, filtered and evaporated to dryness to an oil which was purified by flash column chromatography (Merck 9385 silica), eluting with 80% iso-hexane/ethyl acetate to yield 1-[(-2-phenylvinyl)sulphonyl]-4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]piperazine as a yellow solid. Yield 650 mg (25%)

Workup

customto reach ambient temperature
washWashed with H2O
customseparated off the organic phase
dry with materialDried over MgSO4
filtrationfiltered
customevaporated to dryness to an oil which
customwas purified by flash column chromatography (Merck 9385 silica)
washeluting with 80% iso-hexane/ethyl acetate

Sources & evidence

ORD record: ord-7dcf637165eb438796ab25ddcf0ecb32
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07485644B2

Reaction notes

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