Sodium Hydroxide → 6,6-Bis-(4-fluoro-phenyl)-6-hydroxy-1-[4-(3,4,5,-trimethoxy-benzoyl)-piperazin-1-yl]-hexan-1-one

HRID 496032Notes

Reaction equation

HRID 496032 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)=[CH:9][CH2:10][CH2:11][CH2:12][C:13]([N:15]2[CH2:20][CH2:19][N:18]([C:21](=[O:34])[C:22]3[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=3)[CH2:17][CH2:16]2)=[O:14])=[CH:4][CH:3]=1.[OH-:42].[Na+].[BH4-].[Na+]>C1COCC1.O.C1COCC1.[Hg](OC(C)=O)OC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:35]2[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=2)([OH:42])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([N:15]2[CH2:20][CH2:19][N:18]([C:21](=[O:34])[C:22]3[CH:23]=[C:24]([O:32][CH3:33])[C:25]([O:30][CH3:31])=[C:26]([O:28][CH3:29])[CH:27]=3)[CH2:17][CH2:16]2)=[O:14])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 10460533HCID 10460533, compound

Product 1

HCID 104382506,6-Bis-(4-fluoro-phenyl)-6-hydroxy-1-[4-(3,4,5,-trimethoxy-benzoyl)-piperazin-1-yl]-hexan-1-one

Reagents, catalysts & solvents 3

HCID 16683746DiacetyloxymercuryCatalystHCID 8028TetrahydrofuranSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 6,6-bis-(4-fluoro-phenyl)-1-[4-(3,4,5,-trimethoxy-benzoyl)-piperazin-1-yl]-hex-5-en-1-one (1.62 g, 2.87 mmol) in dry THF (20 ml) a solution of Hg(OAc)2 (0.9 g, 2.87 mmol) in water:THF (1:1, 6 ml) was added. The mixture was then refluxed overnight. NaOH (3M, 3 ml) was added followed by addition of NaBH4 (54 mg, 1.43 mmol). The mixture was stirred for 4 hrs and separated organic layer was saturated with NaCl

Workup

  1. temperatureThe mixture was then refluxed overnight
  2. customseparated organic layer

Sources & evidence

ORD record
ord-3002759bbada46f285d25b1c7df1f105
Source dataset
uspto-grants-2005_09
Patent number
US06943168B2

Reaction notes

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