Boron Trichloride → HCID 70873516, compound

HRID 2172198Notes

Reaction equation

HRID 2172198 reaction equation
B(Cl)(Cl)Cl.C([O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:24][CH2:23][C:22]([O:29][CH3:30])([C:25]([F:28])([F:27])[F:26])[CH2:21][CH2:20]2)=[CH:15][CH:14]=1)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>ClCCl>[CH3:30][O:29][C:22]1([C:25]([F:28])([F:26])[F:27])[CH2:23][CH2:24][N:19]([C:16]2[CH:17]=[CH:18][C:13]([OH:12])=[CH:14][CH:15]=2)[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 25135Boron TrichlorideHCID 516892Sodium BicarbonateHCID 70873556HCID 70873556, compound

Product 1

HCID 70873516HCID 70873516, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron trichloride (1 M dichloromethane solution, 2.3 ml) was added to a solution (50 ml) of 1-(4-benzyloxyphenyl)-4-methoxy-4-trifluoromethylpiperidine (0.7 g) in dichloromethane (50 ml) at 0° C. and stirred for 20 minutes. A sodium hydrogen carbonate aqueous solution was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was washed with water and dried over sodium sulfate. The result was concentrated under reduced pressure, and the residue was washed with diethylether and then dried to afford the title compound as a pale yellow powder (508 mg).

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationThe result was concentrated under reduced pressure
  5. washthe residue was washed with diethylether
  6. customdried

Sources & evidence

ORD record
ord-0b3f979e877241bd908792a590492e89
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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