Piperazine → HCID 21073118, compound

HRID 1592716Notes

Reaction equation

HRID 1592716 reaction equation
[F:1][C:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1Br)([F:4])[CH3:3].[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>>[F:1][C:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)([F:4])[CH3:3]

Participants

3

Reactant 2

HCID 4837PiperazineHCID 179523211-Bromo-2-(1,1-difluoroethyl)benzene

Product 1

HCID 21073118HCID 21073118, compound

Procedure

A solution of diethylaminosulfur trifluoride (560 mg, 3.47 mmol, 3 eq) and 2-bromoacetophenone (230 mg, 1.16 mmol, 1.0 eq) was heated to 40° C. for about 72 hours. The solution was diluted with CH2Cl2 and washed with saturated sodium bicarbonate, water, brine, dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography (35 g SiO2, linear gradient 0-10% ethyl acetate/Hexanes, 30 mL/minute, over 30 minutes) afforded about 125 mg (0.57 mmol, 49%) of 2-(1,1-difluoroethyl)-1-bromobenzene. GC/MS (EI): 220 (M+H). 2-(1,1-Difluoroethyl)-1-bromobenzene was coupled to piperazine in a manner similar to Preparation 1A. LRMS (ESI+): 227.2 (M+1)

Sources & evidence

ORD record
ord-63736f80c35c4364a59fae11eddea957
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

Loading…