Boron tribromide → HCID 22990098, compound

HRID 1169373Notes

Reaction equation

HRID 1169373 reaction equation
[CH3:1][N:2]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=1)[CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:1][N:2]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=1)[CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 25134Boron tribromide2×HCID 516892Sodium BicarbonateHCID 22989990HCID 22989990, compound

Product 1

HCID 22990098HCID 22990098, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Into a solution of N-methyl-N-(tetrahydropyran-4-yl)-4-methoxybenzylamine (2.19 g) in dichloromethane (20 ml) was added at −78° C. a solution of boron tribromide in dichloromethane (11 ml). After gradually raising the temperature from −78° C. to room temperature, the resulting mixture was stirred for 2 hours, an additional solution of boron tribromide in dichloromethane (5 ml) was again added thereto, and the resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was mixed with an aqueous solution of sodium bicarbonate under ice cooling and was extracted with dichloromethane, and the extract was concentrated under reduced pressure. Thereto were added 1 N hydrochloric acid and diethyl ether to extract the aqueous layer. The extract was adjusted to pH 8 by adding an aqueous solution of potassium carbonate and was then extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride, was dried (anhydrous magnesium sulfate) and was then concentrated under reduced pressure. The residue was subjected to purification using silica gel column chromatography (ethyl acetate/methanol) to obtain N-methyl-N-(tetrahydropyran-4-yl)-4-hydroxybenzylamine (206 mg) as a light yellow, oily substance.

Workup

  1. temperatureAfter gradually raising the temperature from −78° C. to room temperature
  2. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  3. extractionwas extracted with dichloromethane
  4. concentrationthe extract was concentrated under reduced pressure
  5. additionThereto were added 1 N hydrochloric acid and diethyl ether
  6. extractionto extract the aqueous layer
  7. additionby adding an aqueous solution of potassium carbonate
  8. extractionwas then extracted with ethyl acetate
  9. washThe extract was washed with an aqueous solution of sodium chloride
  10. dry with materialwas dried (anhydrous magnesium sulfate)
  11. concentrationwas then concentrated under reduced pressure
  12. customThe residue was subjected to purification

Sources & evidence

ORD record
ord-c37ad67213924f77977831adf1fe7032
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

Loading…