Potassium Hydroxide → 2-(2-Piperidin-4-ylphenyl)propan-2-ol

HRID 587637Notes

Reaction equation

HRID 587637 reaction equation
[OH:1][C:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]1[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]1)([CH3:4])[CH3:3].[OH-].[K+]>C(O)(C)C.O>[NH:14]1[CH2:15][CH2:16][CH:11]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:2]([OH:1])([CH3:3])[CH3:4])[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 57459608Tert-butyl 4-[2-(1-hydroxy-1-methyl ethyl)phenyl]piperidine-1-carboxylate

Product 1

HCID 574596102-(2-Piperidin-4-ylphenyl)propan-2-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of intermediate D40 (27 g, 5.636 mmol) and KOH (2.433 g, 43.357 mmol) in isopropyl alcohol (13.5 ml) and water (27 ml) was heated at 180° C. under microwave irradiation for 60 min. After cooling to r.t., the mixture was washed with water and NaCl (aqueous saturated solution). The organic phase was dried (Na2SO4) and the solvent evaporated in vacuo. The crude product was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 10% as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate compound D41 as a yellow solid (1.041. g, 84%). M.P. 219.5° C.

Workup

  1. washthe mixture was washed with water and NaCl (aqueous saturated solution)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. customthe solvent evaporated in vacuo
  4. customThe crude product was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 10% as eluent)
  5. customThe desired fractions were collected
  6. concentrationconcentrated in vacuo
  7. customto yield intermediate compound D41 as a yellow solid (1.041. g, 84%)

Sources & evidence

ORD record
ord-fd7ad55c620c4796b71400d54d95b4ce
Source dataset
uspto-grants-2016_01
Patent number
US09226930B2

Reaction notes

Loading…