4-(Benzyloxy)-3-bromobenzaldehyde → 3-Bromo-N-methyl-4-(phenylmethoxy)benzenemethanamine
Reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][C:10]=1[Br:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CN.[C:21]([BH3-])#[N:22].[Na+]>CO>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][NH:22][CH3:21])=[CH:11][C:10]=1[Br:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Procedure
25 g (86 mmol) of 4-benzyloxy-3-bromo-benzaldehyde, 500 ml of methanol, 29 g (430 mmol) of methylamine hydrochloride and 8 g (127 mmol) of sodium cyanoborohydride are introduced into a round-bottomed flask under a stream of nitrogen. The reaction medium is stirred for 48 hours at room temperature. The methanol is evaporated off. The residue is taken up in ethyl acetate and water and then acidified. After separation of the phases once settling has taken place, the aqueous phase is returned to basic pH with sodium hydroxide and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and then evaporated. The residue is purified by chromatography on a column of silica eluted with a dichloromethane/ethanol mixture (9/1). 9.9 g (38%) of the expected product are obtained in the form of a colorless oil.
Workup
- customThe methanol is evaporated off
- customAfter separation of the phases
- extractionextracted with ethyl acetate
- dry with materialThe organic phase is dried over magnesium sulfate
- filtrationfiltered
- customevaporated
- customThe residue is purified by chromatography on a column of silica
- washeluted with a dichloromethane/ethanol mixture (9/1)
Sources & evidence
- ORD record
- ord-53cb573b34a348fe85b54a1bfdd811d1
- Source dataset
- uspto-grants-2005_08
- Patent number
- US06927228B2
Reaction notes
Loading…