Ammonium Chloride → 863111-06-2

HRID 1670760Notes

Reaction equation

HRID 1670760 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)=O)(C)(C)C.[F:15][C:16]1[CH:17]=[C:18]([Mg]Br)[CH:19]=[CH:20][CH:21]=1.[Cl-:24].[NH4+]>O1CCCC1>[ClH:24].[F:15][C:16]1[CH:21]=[C:20]([C:11]2([OH:14])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 178505773HCID 178505773, compound

Product 1

HCID 23149879863111-06-2Yield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1-(tert-Butoxycarbonyl)-4-piperidone (2.19 g) was dissolved in tetrahydrofuran (30 ml) and the mixture was cooled to 0° C. 3-Fluorophenylmagnesiumbromide (Tokyo Chemical Industry CO., LTD., 1M, 13.2 ml) was added and the mixture was stirred for 6 hr. After completion of the reaction, a saturated aqueous ammonium chloride solution was added, and the mixture was extracted three times with ethyl acetate. The organic layer was dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (elution solvent: hexane-ethyl acetate (5:1-2:1)). Then, 4N hydrochloric acid-ethyl acetate (10 ml) was added and the mixture was stirred for 3 hr. Diethyl ether was added and the precipitated solid was collected by filtration to give 4-(3-fluorophenyl)piperidin-4-ol hydrochloride (902 mg, yield 35%).

Workup

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted three times with ethyl acetate
  3. customThe organic layer was dried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (elution solvent: hexane-ethyl acetate (5:1-2:1))
  6. additionThen, 4N hydrochloric acid-ethyl acetate (10 ml) was added
  7. stirringthe mixture was stirred for 3 hr
  8. additionDiethyl ether was added
  9. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-4facead53c424ac6aa79e676eba4397a
Source dataset
uspto-grants-2011_08
Patent number
US07994196B2

Reaction notes

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