Sodium hydride → HCID 59834606, compound

HRID 271569Notes

Reaction equation

HRID 271569 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:5]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1.Br[CH2:25][CH2:26][O:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][O:29]1>CN(C=O)C>[F:3][C:4]1[CH:9]=[C:8]([O:10][CH2:25][CH2:26][O:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][O:29]2)[CH:7]=[CH:6][C:5]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 20785666tert-Butyl 4-(2-fluoro-4-hydroxyphenyl)piperazine-1-carboxylate

Product 1

HCID 59834606HCID 59834606, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of NaH (21.3 mmol) in DMF (50 ml), 4-(2-fluoro-4-hydroxy-phenyl)-piperazine-1-carboxylic acid, tert.-butyl ester (17.8 mmol) is successively added at 0° C. To the mixture, 2-(2-bromoethoxy)-tetrahydro-2H-pyrane (24.9 mmol) is added at 0° C. and the mixture is stirred for 2 h at ambient temperature. The reaction mixture is quenched with ice-water and extracted with AcOEt. The combined extracts are washed with H2O, brine and dried over magnesium sulfate. Chromatography on silica gel using n-hexane, n-hexane:AcOEt=6:1, n-hexane:AcOEt=4:1 gives the desired 4-{2-fluoro-4-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-phenyl}-piperazine-1-carboxylic acid, tert-butyl ester.

Workup

  1. additionis successively added at 0° C
  2. customThe reaction mixture is quenched with ice-water
  3. extractionextracted with AcOEt
  4. washThe combined extracts are washed with H2O, brine
  5. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-87728f36c9104c33abc31a949f241fec
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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