Methanol → HCID 58270902, compound

HRID 1623217Notes

Reaction equation

HRID 1623217 reaction equation
Cl.[Br:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:5][C:4]=1[O:16][CH2:17][CH2:18][O:19]C.B(Br)(Br)Br.CO>ClCCl>[Br:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:5][C:4]=1[O:16][CH2:17][CH2:18][OH:19]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 67000209HCID 67000209, compound

Product 1

HCID 58270902HCID 58270902, compoundYield 116.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-[4-bromo-3-(2-methoxyethoxy)benzyl]piperidine hydrochloride (RE1) (3.00 g, 8.3 mmol) in dichloromethane (100 mL) was cooled in a salt-ice bath. A 1 M solution of boron tribromide in dichloromethane (7.8 mL, 7.8 mmol) was added dropwise thereto at 0° C. in 30 minutes, and the reaction mixture was stirred for 1.5 hours under ice cooling. Methanol (20 mL) was added thereto, and the solvent was distilled off under reduced pressure. A 5% aqueous potassium carbonate solution (50 mL) was added to the obtained concentrated residue, followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (RE2) (3.03 g, quantitative).

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionA 5% aqueous potassium carbonate solution (50 mL) was added to the obtained concentrated residue
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f2fa84b2b33943e6b82dec39523f57ec
Source dataset
uspto-grants-2014_07
Patent number
US08778970B2

Reaction notes

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