Hydrochloric Acid → 3-(3-(3,4-Dichlorophenyl)piperidin-3-YL)propan-1-OL

HRID 394545Notes

Reaction equation

HRID 394545 reaction equation
Cl.O(CC)CC.[Cl:7][C:8]1[CH:9]=[C:10]([C:15]2([CH2:21][CH2:22][CH2:23][O:24]C3CCOCC3)[CH2:20][CH2:19][CH2:18][NH:17][CH2:16]2)[CH:11]=[CH:12][C:13]=1[Cl:14]>CO>[Cl:7][C:8]1[CH:9]=[C:10]([C:15]2([CH2:21][CH2:22][CH2:23][OH:24])[CH2:20][CH2:19][CH2:18][NH:17][CH2:16]2)[CH:11]=[CH:12][C:13]=1[Cl:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 158876543-(3,4-Dichlorophenyl)-3-[3-(tetrahydropyran-4-yloxy)-propyl]-piperidine

Product 1

HCID 109350863-(3-(3,4-Dichlorophenyl)piperidin-3-YL)propan-1-OLYield 84.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of dry HCl.OEt2 was added to a solution of piperidine (7) (20.2 g, 54.36 mmol) in MeOH (200 mL) until pH˜1. The mixture was stirred at room temperature for 30 minutes. Solvent was evaporated, the residue was dissolved in CH2Cl2 (300 mL) and stirred with 1N NaOH (100 mL) for 15 minutes. The solvent was separated, washed with NaHCO3, and dried over MaSO4. The crude oil was purified by flash chromatography (CH2Cl2-MeOH(saturated with NH3)/95:5) to give a white solid (13.25 g, 84.6%).

Workup

  1. customSolvent was evaporated
  2. dissolutionthe residue was dissolved in CH2Cl2 (300 mL)
  3. stirringstirred with 1N NaOH (100 mL) for 15 minutes
  4. customThe solvent was separated
  5. washwashed with NaHCO3
  6. customdried over MaSO4
  7. customThe crude oil was purified by flash chromatography (CH2Cl2-MeOH(saturated with NH3)/95:5)

Sources & evidence

ORD record
ord-41e90a9a6f784b19a2c75047c0480895
Source dataset
uspto-grants-2003_08
Patent number
US06602886B2

Reaction notes

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