Carbon tetrabromide → HCID 22990189, compound
Reaction equation
[CH3:1][N:2]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16]O)=[CH:12][CH:11]=1)[CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:38].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:1][N:2]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][Br:38])=[CH:12][CH:11]=1)[CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Into a solution of N-methyl-N-(tetrahydropyran-4-yl)-4-(hydroxymethyl)benzylamine (0.68 g) and triphenylphosphine (0.91 g) in dichloromethane (10 ml) was added under ice cooling carbon tetrabromide (1.44 g), and the resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was mixed with an aqueous solution of sodium bicarbonate under ice cooling and was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride, was dried (anhydrous magnesium sulfate) and was concentrated under reduced pressure. The residue was subjected to purification using silica gel column chromatography (ethyl acetate/hexane 1/9) and further to washing with diethyl ether/hexane to obtain N-methyl-N-(tetrahydropyran-4-yl)-4-(bromomethyl)benzylamine (687 mg) as a white solid.
Workup
- extractionwas extracted with ethyl acetate
- washThe extract was washed with an aqueous solution of sodium chloride
- dry with materialwas dried (anhydrous magnesium sulfate)
- concentrationwas concentrated under reduced pressure
- customThe residue was subjected to purification
- washfurther to washing with diethyl ether/hexane
Sources & evidence
- ORD record
- ord-7a856e2ca1954b05bb4b766d89f758ec
- Source dataset
- uspto-grants-2003_09
- Patent number
- US06627651B1
Reaction notes
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