Water → 2-[5-Chloro-2-methoxy-4-(piperidin-1-yl)-phenyl]-ethanol

HRID 637670Notes

Reaction equation

HRID 637670 reaction equation
[Cl:1][C:2]1[C:3]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH2:8][C:9](O)=[O:10])[CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[Cl:1][C:2]1[C:3]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH2:8][CH2:9][OH:10])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 541834705-Chloro-2-methoxy-4-(piperidin-1-yl)-phenylacetic acid

Product 1

HCID 202556442-[5-Chloro-2-methoxy-4-(piperidin-1-yl)-phenyl]-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 14.2 g (50 mmole) of 5-chloro-2-methoxy-4-(piperidin-1-yl)-phenylacetic acid in 50 ml of absolute tetrahydrofuran is added dropwise over a period of approximately 15 minutes to a suspension of 1.6 g (42 mmole) of lithium aluminium hydride in 90 ml of absolute tetrahydrofuran. The whole is subsequently stirred for a further 2 hours at 50°. After the addition of 50 ml of water, the whole is filtered over Hyflo and then washed with THF. The solvent is concentrated in a vacuum rotary evaporator and the residue is partitioned between ether and water. The ether phases are combined, dried over sodium sulphate and concentrated in a vacuum rotary evaporator. The residue is chromatographed over silica gel using chloroform/ethyl acetate (1:1) as eluant. Recrystallisation from ether/petroleum ether yields 2-[5-chloro-2-methoxy-4-(piperidin-1-yl)-phenyl]-ethanol having a melting point of 56°-57°.

Workup

  1. filtrationthe whole is filtered over Hyflo
  2. washwashed with THF
  3. concentrationThe solvent is concentrated in a vacuum rotary evaporator
  4. customthe residue is partitioned between ether and water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in a vacuum rotary evaporator
  7. customThe residue is chromatographed over silica gel
  8. customRecrystallisation from ether/petroleum ether

Sources & evidence

ORD record
ord-5d3878ad98084d029d21ad2e4c389d19
Source dataset
uspto-grants-1985_12
Patent number
US04558043

Reaction notes

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