Methyl vinyl sulfone → 2,2-Dimethyl-1-(2-(methylsulfonyl)ethyl)piperazine

HRID 1922647Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][NH:11][C:10]([CH3:15])([CH3:14])[CH2:9]1)=O)(C)(C)C.[CH:16]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH2:17]>CO>[CH3:21][S:18]([CH2:16][CH2:17][N:11]1[CH2:12][CH2:13][NH:8][CH2:9][C:10]1([CH3:14])[CH3:15])(=[O:20])=[O:19]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 3,3-dimethylpiperazine-1-carboxylic acid tert-butyl ester (500 mg, 2.33 mmol) and methyl vinyl sulfone (510 μL, 619 mg, 5.83 mmol) in MeOH (15 mL) was heated to 65° C. for 5.5 h then stirred at room temperature for 96 h. The reaction mixture was concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, MeOH:DCM, 0-3%) affording 1-(2-(Methanesulfonyl)ethyl)-2,2-dimethylpiperazine as a white waxy solid (550 mg, 74%). 1H NMR (CDCl3, 300 MHz): δ 3.47-3.40 (m, 2H); 3.15 (s, 2H); 3.09 (t, J=6.4 Hz, 2H); 3.03 (s, 3H); 2.89 (t, J=6.4 Hz, 2H); 2.58-2.50 (m, 2H); 1.45 (s, 9H); 1.04 (s, 6H).

Workup

concentrationThe reaction mixture was concentrated in vacuo
customThe resulting residue was purified by column chromatography (Si—PCC, MeOH:DCM, 0-3%)

Sources & evidence

ORD record: ord-d3dc2c58ca9949169e69f7a6fa85ae86
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173650B2

Reaction notes

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