Hydrochloric Acid → 1-Benzyl-4-[4-(2-hydroxy-ethyl)-phenyl]-piperidin-4-ol

HRID 1858628Notes

Reaction equation

HRID 1858628 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][O:23]C3CCCCO3)=[CH:17][CH:16]=2)([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(=O)([O-])O.[Na+]>CO>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][OH:23])=[CH:19][CH:20]=2)([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 22127334(RS)-1-benzyl-4-[4-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl]-piperidin-4-ol

Product 1

HCID 149034381-Benzyl-4-[4-(2-hydroxy-ethyl)-phenyl]-piperidin-4-olYield 84.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 78 g (197 mmol) of (RS)-1-benzyl-4-[4-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl]-piperidin-4-ol in 400 ml of methanol was treated with 470 ml of 2N hydrochloric acid and stirred at room temperature for 5 hours. For the working-up, the reaction solution was poured into 1500 ml of saturated sodium hydrogen carbonate solution and subsequently extracted three times with 1000 ml of ethyl acetate each time. The combined organic phases were dried over sodium sulphate and evaporated under reduced pressure. For purification of the crude substance, a flash chromatography on silica gel using a 95:5 mixture of methylene chloride and methanol as the eluent was carried out. There were obtained 51.6 g (84% of theory) of 1-benzyl-4-[4-(2-hydroxy-ethyl)-phenyl]-piperidin-4-ol as a yellowish solid; MS: 312 (M+H)+.

Workup

  1. extractionsubsequently extracted three times with 1000 ml of ethyl acetate each time
  2. dry with materialThe combined organic phases were dried over sodium sulphate
  3. customevaporated under reduced pressure
  4. customFor purification of the crude substance
  5. additiona flash chromatography on silica gel using a 95:5 mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-64b277fa0e304e648e023f289ac4c43c
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

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