Phenyl glycidyl ether → N-[4-[4-(2-hydroxy-3-phenoxypropyl)piperazin-1-yl]phenyl]methanesulfonamide

HRID 728829Notes

Reaction equation

CS(O)(=O)=O.[N:6]1([C:12]2[CH:17]=[CH:16][C:15]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:14][CH:13]=2)[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.[O:23]1[CH:25]([CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:24]1.C[O-].[Na+]>CO>[OH:23][CH:25]([CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:24][N:9]1[CH2:10][CH2:11][N:6]([C:12]2[CH:13]=[CH:14][C:15]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:16][CH:17]=2)[CH2:7][CH2:8]1

Participants

Conditions

Temperature: 60 °C

Procedure

Suspend a mixture of 20.0 g (56.9 mmol) of N-[4-(piperazin-1-yl)phenyl]methanesulfonamide methanesulfonate, 7.68 mL (56.9 mmol) of 1,2-epoxy-3-phenoxypropane and 3.07 g (56.9 mmol) of sodiummethoxide in 800 mL of 90% aqueous methanol and warm to 60° C. for 18 h. After 18 h, filter the precipitate and wash this precipitate with 100 mL of water and 100 mL of methanol. Suspend this solid precipitate in 500 mL of methanol and reflux for 1 h. After 1 h, cool the suspension to room temperature and filter to obtain the title compound.

Workup

filtrationfilter the precipitate
washwash this precipitate with 100 mL of water and 100 mL of methanol
temperaturereflux for 1 h
waitAfter 1 h
temperaturecool the suspension to room temperature
filtrationfilter

Sources & evidence

ORD record: ord-e08eaf4769d64f228a4ae5d48c13dfb2
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05051423

Reaction notes

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