1-Bromo-2-Chloroethane → 1-(2-Chloroethyl)-4-(methylsulfonyl)piperazine

HRID 85727

Reaction equation

HRID 85727 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)(=[O:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH2:19][Cl:20]>C(#N)C>[Cl:20][CH2:19][CH2:18][N:8]1[CH2:9][CH2:10][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 7091611-(Methylsulfonyl)piperazine

Product 1

HCID 201583501-(2-Chloroethyl)-4-(methylsulfonyl)piperazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(methylsulfonyl)piperazine (250 mg, 1.522 mmol), potassium carbonate (1262 mg, 9.13 mmol) and 1-bromo-2-chloroethane (1092 mg, 7.61 mmol) in acetonitrile (5 mL) was stirred for 6 hours at room temperature. LCMS indicated the formation of desired product. The reaction mixture was filtered to remove the white precipitate, then quenched with distilled water (10 mL), extracted with ethyl acetate (3×8 mL), the extracts were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to provide the clean desired product as white solid (100 mg, 29%). LCMS: m/e 227.15 (M+H)+, 1.21 min (method 10).

Sources & evidence

ORD record
ord-19ad2a3a85a444e3ba8bdb52476b5267
Source dataset
uspto-grants-2014_09
Patent number
US08846647B2

Linked notes

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