Isovaleryl chloride → 4-(2,5-Difluoro-4-methoxyphenyl)-1-phenethylsulfonylpiperazine

HRID 269950Notes

Reaction equation

HRID 269950 reaction equation
Cl.Cl.COC1C=CC(N2CCNCC2)=CC=1.C(Cl)(=O)CC(C)C.[F:24][C:25]1[CH:30]=[C:29]([O:31][CH3:32])[C:28]([F:33])=[CH:27][C:26]=1[N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.[CH2:40]([S:48](Cl)(=[O:50])=[O:49])[CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>>[F:24][C:25]1[CH:30]=[C:29]([O:31][CH3:32])[C:28]([F:33])=[CH:27][C:26]=1[N:34]1[CH2:39][CH2:38][N:37]([S:48]([CH2:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)(=[O:50])=[O:49])[CH2:36][CH2:35]1

Participants

5

Reactant 4

HCID 66054Isovaleryl chlorideHCID 27237001-(4-Methoxyphenyl)-piperazine, dihydrochlorideHCID 27603742-Phenylethane-1-sulfonyl chlorideHCID 231114921-(2,5-Difluoro-4-methoxyphenyl)piperazine

Product 1

HCID 231114704-(2,5-Difluoro-4-methoxyphenyl)-1-phenethylsulfonylpiperazineYield 101.3%

Procedure

Production Example 3 was repeated except that 1-(4-methoxyphenyl)piperazine dihydrochloride and isovaleryl chloride were replaced with 1-(2,5-difluoro-4-methoxyphenyl)-piperazine (228 mg) and phenethylsulfonyl chloride (409 mg), respectively, to provide crude 4-(2,5-difluoro-4-methoxyphenyl)-1-phenethylsulfonylpiperazine (401 mg).

Sources & evidence

ORD record
ord-32b52a5ec05e46bea8ee38a9779b3e1a
Source dataset
uspto-grants-2008_11
Patent number
US07449466B2

Reaction notes

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