Aluminium lithium hydride → 2-(1-(4-Bromophenyl) piperidin-4-yloxy)ethanol

HRID 57593Notes

Reaction equation

HRID 57593 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([O:14][CH2:15][C:16](OC(C)(C)C)=[O:17])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:9][CH2:10][CH:11]([O:14][CH2:15][CH2:16][OH:17])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86717376Tert-butyl 2-(1-(4-bromophenyl)piperidin-4-yloxy)acetate

Product 1

HCID 710936842-(1-(4-Bromophenyl) piperidin-4-yloxy)ethanolYield 86.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl 2-(1-(4-bromophenyl)piperidin-4-yloxy)acetate (3.08 g, 8.3 mmol) in THF (20 mL) at −10° C. under nitrogen was added lithium aluminum hydride (0.57 g, 15 mmol). After 2 hours, the reaction mixture was quenched by sequential addition of water (0.6 mL), 15 percent aqueous sodium hydroxide solution (1.8 mL) and water (0.6 mL). The resulting mixture was filtered and concentrated under vacuum to provide the crude 2-(1-(4-bromophenyl) piperidin-4-yloxy)ethanol 2.16 g. MS (m/z): 302 (M+2)+

Workup

  1. customthe reaction mixture was quenched by sequential addition of water (0.6 mL), 15 percent aqueous sodium hydroxide solution (1.8 mL) and water (0.6 mL)
  2. filtrationThe resulting mixture was filtered
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-fd663e3cf4264f3d9e23bd65e43f9796
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

Loading…