Dimethyl Sulfoxide → HCID 68961411, compound

HRID 2110160Notes

Reaction equation

HRID 2110160 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[Cl:9].[CH3:10][C@H:11]1[CH2:16][NH:15][CH2:14][C@@H:13]([CH3:17])[NH:12]1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O.C(#N)C.C1(C)C=CC=CC=1>[ClH:9].[Br:1][C:2]1[CH:7]=[C:6]([N:15]2[CH2:14][C@H:13]([CH3:17])[NH:12][C@H:11]([CH3:10])[CH2:16]2)[CH:5]=[CH:4][C:3]=1[Cl:9]

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 27732632-Bromo-1-chloro-4-fluorobenzeneHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazine

Product 1

HCID 68961411HCID 68961411, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

2-Bromo-1-chloro-4-fluorobenzene (2.1 g, 10 mmol), cis-2,6-dimethylpiperazine (1.4 g, 12 mmol), potassium carbonate (3.3 g, 24 mmol), DMSO (10 mL), and PhMe (2 mL) were heated at 150° C. under nitrogen for 7 h. Acetonitrile (2 mL; to keep subliming piperazine in reaction) was added and the reaction was heated for an additional 12 h. The cooled mixture was poured into water (150 mL) and extracted with diethyl ether (50 mL×2). The combined extracts were washed with water (100 mL) and brine (100 mL). Addition of HCl (5 mL, 4N in dioxane) and filtration provided 1-(3-bromo-4-chlorophenyl)-cis-3,5-dimethylpiperazine hydrochloride as a white solid: MS (ESI): 243.5 (M+H).

Workup

  1. temperaturethe reaction was heated for an additional 12 h
  2. extractionextracted with diethyl ether (50 mL×2)
  3. washThe combined extracts were washed with water (100 mL) and brine (100 mL)
  4. additionAddition of HCl (5 mL, 4N in dioxane) and filtration

Sources & evidence

ORD record
ord-097d951b27414b7da68ead19a4e4b6c6
Source dataset
uspto-grants-2009_04
Patent number
US07517884B2

Reaction notes

Loading…