Diethyl Ether → Piperidine, 3-[(3,4-difluorophenyl)methoxy]-

HRID 1727222Notes

Reaction equation

HRID 1727222 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][O:10][CH:11]2[CH2:16][CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12]2)[CH:5]=[CH:6][C:7]=1[F:8].C(OCC)C>CO>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][O:10][CH:11]2[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 69055376HCID 69055376, compound

Product 1

HCID 42844093Piperidine, 3-[(3,4-difluorophenyl)methoxy]-Yield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
2.5 °C

Procedure

1,1-dimethylethyl 3-{[(3,4-difluorophenyl)methyl]oxy}piperidine-1-carboxylate (Preparation 145, 3.38 g, 10.3 mmol) was dissolved in methanol (100 ml) and cooled 5 to 0° C., hydrogen chloride gas was bubbled into the reaction mixture for 3-5 min. The reaction mixture was concentrated in vacuo to give an oil, upon tituration with diethyl ether a white solid formed. The solid was separated by filtration to give the title compound (1.78 g, 65%) as the hydrochloride salt.

Workup

  1. customhydrogen chloride gas was bubbled into the reaction mixture for 3-5 min
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto give an oil
  4. customThe solid was separated by filtration

Sources & evidence

ORD record
ord-41a4af0135cf4fc59b6696bef0b8a3d6
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

Loading…