Benzene, 1-(chloromethyl)-2-fluoro- → N-(2-Fluorophenylmethyl)-3-hydroxy-3-phenylpropylamine

A mixture of 3-hydroxy-3-phenylpropylamine (7.0 g, 46 mM) and 2,2,6,6-tetramethylpiperidine (7.9 ml, 46 mM) in acetonitrile (100 ml) was treated with a solution of o-fluorobenzyl chloride (6.75 g, 46 mM) in acetonitrile (10 ml). After 24 hours the resulting precipitate was removed by filtration and washed with acetonitrile (2×10 ml). The combined filtrate and washings were evaporated under reduced pressure and the residue partitioned between 2 N hydrochloric acid (50 ml) and ether (100 ml). The aqueous layer was basified by extracted with ether, the ether extracts dried and evaporated. Chromatography on Grade 3 silica using 2% methanol in chloroform as eluant followed by distillation gave the title compound (6.3 g) b.p. 156°-160° C. (0.2 mbar). Found: C, 73.9; H, 7.1; N, 5.2%; C16H18FNO requires: C, 74.1; H, 7.0; N, 5.4%.

1. customAfter 24 hours the resulting precipitate was removed by filtration
2. washwashed with acetonitrile (2×10 ml)
3. customThe combined filtrate and washings were evaporated under reduced pressure
4. customthe residue partitioned between 2 N hydrochloric acid (50 ml) and ether (100 ml)
5. extractionby extracted with ether
6. dry with materialthe ether extracts dried
7. customevaporated
8. distillationChromatography on Grade 3 silica using 2% methanol in chloroform as eluant followed by distillation

ORD record

ord-29f469f5972b4b80aee95820eb9528a5

Source dataset

uspto-grants-1982_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04318909