Water → 1-(4-Fluorophenyl)-4-(methylsulfonyl)piperazine

HRID 1008767Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 1-(4-fluorophenyl)piperazine dihydrochloride (2.53 g; 10.0 mmol; 1.0 eq.) in anhydrous DCM (50 mL) was added TEA (3.33 g; 33.0 mmol; 3.3 eq.) and the resulting mixture was chilled at 0° C. A 1N solution of methanesulfonyl chloride (1.26 g; 11.0 mmol; 1.1 eq.) in DCM (11 mL) was added dropwise. After 20 min at 0° C., the reaction mixture was stirred at rt for 3 h. Water was added and the mixture extracted with DCM. The combined organic layers were washed with an aqueous saturated solution of NaHCO3, water, brine then dried over MgSO4, filtered and evaporated to give a white powder. Crystallization from EtOAc gave a white solid (1.98 g, 76% yield). HPLC, Rt: 2.3 min (purity: 100%). 1H NMR (CDCl3) δ: 7.08-6.83 (m, 4H), 3.41 (m, 4H), 3.22 (m, 4H), 2.85 (s, 3H).

Workup

extractionthe mixture extracted with DCM
washThe combined organic layers were washed with an aqueous saturated solution of NaHCO3, water, brine
dry with materialthen dried over MgSO4
filtrationfiltered
customevaporated
customto give a white powder
customCrystallization from EtOAc

Sources & evidence

ORD record: ord-baa28623bf974818992271b11b4c1e72
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973039B2

Reaction notes

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