Sodium Hydroxide → 4-(5-Fluoro-2-methoxyphenyl)piperidine

HRID 1978832Notes

Reaction equation

HRID 1978832 reaction equation
C([N:3]1[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=2[O:16][CH3:17])[CH2:5][CH2:4]1)=O.[OH-].[Na+]>Cl.CO>[F:15][C:13]1[CH:12]=[CH:11][C:10]([O:16][CH3:17])=[C:9]([CH:6]2[CH2:7][CH2:8][NH:3][CH2:4][CH2:5]2)[CH:14]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15512821HCID 15512821, compound2×

Product 1

HCID 155128224-(5-Fluoro-2-methoxyphenyl)piperidine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

The crude product of 1-formyl-4-(5-fluoro-2-methoxy-phenyl)-piperidine (0.80 g, 3.4 mmole) (Intermediate 3) was dissolved in HCl (16 mL, 0.5 N) and MeOH (5 mL), and the mixture was brought to reflux for 16 hours. The mixture was cooled to room temperature and basified with NaOH (2.5 N), and extracted with EtOAc (3×25 mL) to give 4-(5-fluoro-2-methoxy-phenyl)-piperidine which was used directly without further purification.

Workup

  1. temperatureto reflux for 16 hours
  2. extractionextracted with EtOAc (3×25 mL)

Sources & evidence

ORD record
ord-3fbb02d2f0d8464dbf66c1607c6496b9
Source dataset
uspto-grants-2001_05
Patent number
US06239126B1

Reaction notes

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