Sodium sulfate decahydrate → 1-Methyl-3-(2-(4-(3-methoxyphenyl)butyl)phenoxymethyl)piperidine

HRID 743329Notes

Reaction equation

HRID 743329 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=2)[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+]>O1CCCC1>[CH3:33][O:32][C:28]1[CH:27]=[C:26]([CH2:25][CH2:24][CH2:23][CH2:22][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][CH2:14][CH:10]2[CH2:11][CH2:12][CH2:13][N:8]([CH3:6])[CH2:9]2)[CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 106473391-t-Butoxycarbonyl-3-{2-[4-(3-methoxyphenyl)butyl]phenoxymethyl}piperidineHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 100012501-Methyl-3-(2-(4-(3-methoxyphenyl)butyl)phenoxymethyl)piperidineYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.70 g of 1-t-butoxycarbonyl-3-{2-[4-(3-methoxyphenyl)butyl]phenoxymethyl}piperidine [prepared as described in Example 82(a)] in 25 ml of tetrahydrofuran was added dropwise to a mixture of 0.450 g of lithium aluminum hydride in 30 ml of tetrahydrofuran, whilst ice-cooling and stirring, and the mixture was stirred at room temperature for 30 minutes and then stirred whilst heating under reflux for 2 hours. At the end of this time, the reaction mixture was cooled, and sodium sulfate decahydrate was added to the mixture to decompose excess lithium aluminium hydride. Insoluble materials were removed by filtration, and the filtrate was concentrated by distillation under reduced pressure. The resulting oil 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 2.10 g (yield 96%) of the title compound as a colorless oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. stirringstirred
  4. temperaturewhilst heating
  5. temperatureunder reflux for 2 hours
  6. temperatureAt the end of this time, the reaction mixture was cooled
  7. customInsoluble materials were removed by filtration
  8. concentrationthe filtrate was concentrated by distillation under reduced pressure
  9. customThe resulting oil was purified by column chromatography through silica gel
  10. additionby volume mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-098ea59c9bd44c91a655fbcf3cda29be
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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