Water → (+/-)-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-2-[2-hydroxy-2-[4-(trifluoromethoxy)-phenyl]ethyl]-5-methyl-3H-1,2,4-triazol-3-one

HRID 266070Notes

Reaction equation

HRID 266070 reaction equation
CC([Si](C)(C)[O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([N:25]4[C:29]([CH3:30])=[N:28][N:27]([CH2:31][CH:32]([OH:44])[C:33]5[CH:38]=[CH:37][C:36]([O:39][C:40]([F:43])([F:42])[F:41])=[CH:35][CH:34]=5)[C:26]4=[O:45])=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.O>ClCCl>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([N:25]4[C:29]([CH3:30])=[N:28][N:27]([CH2:31][CH:32]([OH:44])[C:33]5[CH:38]=[CH:37][C:36]([O:39][C:40]([F:41])([F:43])[F:42])=[CH:35][CH:34]=5)[C:26]4=[O:45])=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 19032415(+/-)-4-[4-[4-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-2-[2-hydroxy-2-[4-(trifluoromethoxy)phenyl]ethyl]-5-methyl-3H-1,2,4-triazol-3-one

Product 1

HCID 19032431(+/-)-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-2-[2-hydroxy-2-[4-(trifluoromethoxy)-phenyl]ethyl]-5-methyl-3H-1,2,4-triazol-3-oneYield 58.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (±)-4-[4-[4-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-2-[2-hydroxy-2-[4-(trifluoromethoxy)phenyl]ethyl]-5-methyl-3H-1,2,4-triazol-3-one (0.0043 mol) was dissolved in dichloromethane (100 ml) upon stirring. A solution of tetrabutylammonium fluoride in tetrahydrofuran (0.0045 mol) was added and the mixture was stirred at room temperature for 15 minutes. Water was added and the mixture was stirred for 30 minutes. The precipitate was filtered off, dried and crystallized from n-butanol, yielding 1.1 g (58.2%) of (±)-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-2-[2-hydroxy-2-[4-(trifluoromethoxy)-phenyl]ethyl]-5-methyl-3H-1,2,4-triazol-3-one; mp. 230.6° C. (comp. 36).

Workup

  1. stirringthe mixture was stirred at room temperature for 15 minutes
  2. stirringthe mixture was stirred for 30 minutes
  3. filtrationThe precipitate was filtered off
  4. customdried
  5. customcrystallized from n-butanol

Sources & evidence

ORD record
ord-8603b9de42754e9d88ba981e2ea7f37b
Source dataset
uspto-grants-1997_07
Patent number
US05650411

Reaction notes

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