1-t-Butoxycarbonyl-2-(2-{2-[2-(4-ethylphenyl)ethyl]phenoxy}ethyl)piperidine → 2-(2-{2-[2-(4-Ethylphenyl)ethyl]phenoxy}ethyl)-1-methylpiperidine

HRID 743309Notes

Reaction equation

HRID 743309 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][C:28]([CH2:31][CH3:32])=[CH:27][CH:26]=1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:31]([C:28]1[CH:27]=[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]=1)[CH3:32]

Participants

4

Reactant 2

HCID 194238691-t-Butoxycarbonyl-2-(2-{2-[2-(4-ethylphenyl)ethyl]phenoxy}ethyl)piperidineHCID 21226445Aluminium lithium hydride

Product 1

HCID 194238792-(2-{2-[2-(4-Ethylphenyl)ethyl]phenoxy}ethyl)-1-methylpiperidineYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following a procedure similar to that described in Example 38(a), 1.00 g of 1-t-butoxycarbonyl-2-(2-{2-[2-(4-ethylphenyl)ethyl]phenoxy}ethyl)piperidine [prepared as described in Example 69(a)] were reacted with 0.173 g of lithium aluminum hydride dispersed in 20 ml of tetrahydrofuran. The mixture was then worked up as described in Example 38(a), 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 0.650 g (yield 81%) of the title compound as a colorless oil.

Workup

  1. customthe crude product thus obtained
  2. customwas purified by column chromatography through silica gel using a 10:1
  3. additionby volume mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-107aaf4eee1d44d181f841c1e2ced6b7
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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