1-t-Butoxycarbonyl-4-(2-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}ethyl)piperidine → 4-(2-{2-[2-(3-Methoxyphenyl)ethyl]phenoxy}ethyl)-1-methylpiperidine

HRID 743276Notes

Reaction equation

HRID 743276 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=2)[CH2:10][CH2:9]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:11]2[CH2:10][CH2:9][N:8]([CH3:6])[CH2:13][CH2:12]2)[CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 107655341-t-Butoxycarbonyl-4-(2-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}ethyl)piperidineHCID 21226445Aluminium lithium hydride

Product 1

HCID 105005754-(2-{2-[2-(3-Methoxyphenyl)ethyl]phenoxy}ethyl)-1-methylpiperidineYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following a procedure similar to that described in Example 38, 2.15 g of 1-t-butoxycarbonyl-4-(2-{2-[2(3-methoxyphenyl)ethyl]phenoxy}ethyl)piperidine [prepared as described in Example 53 (a)] were reacted with 0.371 g of lithium aluminum hydride dispersed in 40 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 1.56 g (yield 90%) of 4-(2-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}ethyl)-1-methylpiperidine as an 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-9fcd99ce3e80495da60236568643d767
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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