Water → Tert-butyl 4-(methylsulfonyl)piperazine-1-carboxylate

HRID 2377295Notes

Reaction equation

[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23].O>ClCCl>[CH3:21][S:22]([N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]1)(=[O:24])=[O:23]

Participants

Conditions

Temperature: 0 °C

Procedure

Tert-butyl piperazine-1-carboxylate (5.3 g, 28.5 mmol) and triethylamine (6 mL) were combined in dichloromethane (60 mL) and treated with methanesulfonyl chloride (2.6 mL, 33.6 mmol) at about 0° C. The mixture was stirred at about 0° C. for about 30 min, water (100 mL) was added and the mixture was extracted with dichloromethane. The combined organic layers were dried over MgSO4, filtered and concentrated under vacuum to provide the desired product. 1H NMR (300 MHz, CDCL3): δ 1.42 (s, 9H), 2.80 (s, 3H), 3.18 (t, J=7.0 Hz, 4H), 3.56 (t, J=7.0 Hz, 4H).

Workup

extractionthe mixture was extracted with dichloromethane
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-d1a49c68c04945619e81900494bb4303
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07468371B2

Reaction notes

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