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 2N hydrochloric acid (50 ml) and ether (100 ml). The aqueous layer was basified and 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).

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 2N hydrochloric acid (50 ml) and ether (100 ml)
5. extractionextracted 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-868acbd05e6a4849a9c7572a5f4568ed

Source dataset

uspto-grants-1986_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04626522