Sodium sulfate decahydrate → 4-{2-[2-(3-Methoxyphenyl)ethyl]phenoxy}-1-methylpiperidine

HRID 743250Notes

Reaction equation

HRID 743250 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].[H-]>O1CCCC1>[CH3:30][O:29][C:25]1[CH:24]=[C:23]([CH2:22][CH2:21][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][CH:11]2[CH2:12][CH2:13][N:8]([CH3:6])[CH2:9][CH2:10]2)[CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 62649Sodium sulfate decahydrateHCID 166653HydrideHCID 106215801-t-Butoxycarbonyl-4-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}piperidineHCID 21226445Aluminium lithium hydride

Product 1

HCID 105706074-{2-[2-(3-Methoxyphenyl)ethyl]phenoxy}-1-methylpiperidineYield 57.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 482 mg of 1-t-butoxycarbonyl-4-{2-[2-(3-methoxylphenyl)ethyl]phenoxy]piperidine (prepared in a similar manner to that described in Example 37) in 5 ml of tetrahydrofuran was added dropwise to a dispersion of 44.5 mg of lithium aluminum hydride in 5 ml of tetrahydrofuran, whilst stirring. After the addition was complete, the reaction mixture was heated under reflux for 1 hour and then cooled. Sufficient sodium sulfate decahydrate was then added to the reaction mixture, in order to decompose any excess of the hydride, after which the mixture was stirred for about 30 minutes. Insoluble materials were filtered off, and then the filtrate was freed from the solvent by distillation under reduced pressure. The resulting oily residue was purified by column chromatography through silica gel, using a 10:1 by volume mixture of methylene chloride and methanol as the eluent, to give 220 mg (yield 57%) of the title compound as a colorless oil.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux for 1 hour
  4. temperaturecooled
  5. stirringafter which the mixture was stirred for about 30 minutes
  6. filtrationInsoluble materials were filtered off
  7. distillationthe filtrate was freed from the solvent by distillation under reduced pressure
  8. customThe resulting oily residue was purified by column chromatography through silica gel
  9. additionby volume mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-a0ec0d9bd3d94edaa2249b9a4e4c402f
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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