Benzene, 1-(chloromethyl)-2-fluoro- → N-(2-fluorophenylmethyl)-3-hydroxy-N-methyl-3-phenylpropylamine
Reaction equation
[OH:1][CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][CH2:4][NH:5][CH3:6].CC1(C)CCCC(C)(C)N1.[F:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26]Cl>C(#N)C>[F:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26][N:5]([CH2:4][CH2:3][CH:2]([OH:1])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH3:6]Participants
5
Procedure
A mixture of 3-hydroxy-N-methyl-3-phenylpropylamine (8.3 g, 50 mM), 2,2,6,6-tetramethylpiperidine (8.4 ml, 50 mM), o-fluorobenzyl chloride (7.25 g, 50 mM) and acetonitrile (100 ml) was stirred for 24 hours at ambient temperature. The resulting precipitate was removed by filtration, the precipitate washed with acetonitrile and the combined filtrate and washings evaporated under reduced pressure. The residue was partitioned between 2N hydrochloric acid (100 ml) and ether (100 ml), the aqueous layer basified and extracted with ether (2×100 ml). The ether extract was dried and the solvent removed under reduced pressure to yield an oil (10.3 g). Distillation gave the title compound b.p. 160°-2° C./0.6 mbar.
Workup
- customThe resulting precipitate was removed by filtration
- washthe precipitate washed with acetonitrile
- customthe combined filtrate and washings evaporated under reduced pressure
- customThe residue was partitioned between 2N hydrochloric acid (100 ml) and ether (100 ml)
- extractionextracted with ether (2×100 ml)
- extractionThe ether extract
- customwas dried
- customthe solvent removed under reduced pressure
Sources & evidence
- ORD record
- ord-8d869784870844408ce5698be500f924
- Source dataset
- uspto-grants-1986_12
- Patent number
- US04626522
Reaction notes
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