1-t-Butoxycarbonyl-2-(2-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}ethyl)piperidine → 2-(2-{2-[2-(3-Methoxyphenyl)ethyl]phenoxy}ethyl)-1-methylpiperidine

HRID 743264Notes

Reaction equation

HRID 743264 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:32][O:31][C:27]1[CH:26]=[C:25]([CH2:24][CH2:23][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][CH2:15][CH2:14][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][N:8]2[CH3:6])[CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 105750741-t-Butoxycarbonyl-2-(2-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}ethyl)piperidineHCID 21226445Aluminium lithium hydride

Product 1

HCID 106680932-(2-{2-[2-(3-Methoxyphenyl)ethyl]phenoxy}ethyl)-1-methylpiperidineYield 53.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following a procedure similar to that described in Example 38, 1.70 g of 1-t-butoxycarbonyl-2-(2-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}ethyl)piperidine [prepared as described in Example 47(a)] were reacted with a dispersion of 0.294 g of lithium aluminum hydride in 30 ml of tetrahydrofuran. The mixture was then worked up as described in Example 38, and the crude product thus obtained 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 0.730 g (yield 53%) of the title compound as a colorless oil.

Workup

  1. customthe crude product thus obtained
  2. customwas purified by column chromatography through silica gel
  3. additionby volume mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-aba2aa00efb049aca2032ec6b7004603
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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