Water → 2-[1-[4-(2-Fluorophenoxymethyl)piperidino]ethyl]-3-methoxypyrazine

HRID 606248Notes

Reaction equation

HRID 606248 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[O:4][CH2:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.[C:16]([C:19]1[C:24]([O:25][CH3:26])=[N:23][CH:22]=[CH:21][N:20]=1)(=O)[CH3:17].[BH4-].[Na+].O>CO.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].C(OCC)(=O)C>[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[O:4][CH2:5][CH:6]1[CH2:7][CH2:8][N:9]([CH:16]([C:19]2[C:24]([O:25][CH3:26])=[N:23][CH:22]=[CH:21][N:20]=2)[CH3:17])[CH2:10][CH2:11]1

Participants

8

Reactant 4

HCID 962WaterHCID 5398321-(3-Methoxy-2-pyrazinyl)ethanoneHCID 4311764Sodium borohydrideHCID 171780514-[(2-Fluorophenoxy)methyl]piperidine

Product 1

HCID 222483652-[1-[4-(2-Fluorophenoxymethyl)piperidino]ethyl]-3-methoxypyrazineYield 11%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 11026Titanium isopropoxideSolvent

Procedure

After dissolving 1.09 g of 4-(2-fluorophenoxymethyl)piperidine in 15 ml of methanol, 1.53 ml of titanium (IV) tetraisopropoxide and 400 mg of 2-acetyl-3-methoxypyrazine [CAS No. 56343-40-9] were added and the mixture was stirred overnight at room temperature. The reaction solution was cooled on ice, 148 mg of sodium borohydride was added and the mixture was stirred for 5 hours at room temperature. Water and ethyl acetate were added to the reaction solution and the mixture was filtered with celite. The filtrate was extracted with ethyl acetate and the extract was washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by NH silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (100 mg, 11% yield).

Workup

  1. addition56343-40-9] were added
  2. additionwas added
  3. stirringthe mixture was stirred for 5 hours at room temperature
  4. filtrationthe mixture was filtered with celite
  5. extractionThe filtrate was extracted with ethyl acetate
  6. washthe extract was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was purified by NH silica gel column chromatography (solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-81cf126bcc0f4fd695df60207e1dba84
Source dataset
uspto-grants-2011_03
Patent number
US07915274B2

Reaction notes

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