Water → HCID 70561822, compound

A solution of cis-1-methyl-5-phenyl-3-piperidinol (2.03 g) in THF (20 ml) was treated with 60% sodium hydride dispersion in oil (480 mg) and heated 15 min. at reflux. The mixture was cooled to room temperature and treated with methyl tosylate (1.86 g) in THF (5 ml). The reaction mixture was stirred for 1 hour at ambient temperature, treated with water (5 ml) and the solvents removed under reduced pressure. The residue was partitioned between water (100 ml) and ether (100 ml). The organic phase was dried over magnesium sulphate and the solvent removed under reduced pressure. The resulting oil was triturated with cyclohexane (10 ml) and the resulting crystals (300 mg; unchanged starting material) removed by filtration. The mother liquors were evaporated under reduced pressure and the resulting gum converted to the fumarate which was recrystallised from methanol/ethyl acetate to give the title compound as the sesquifumarate (500 mg) Mpt. 152°-4°

1. temperatureheated 15 min.
2. temperatureat reflux
3. customthe solvents removed under reduced pressure
4. customThe residue was partitioned between water (100 ml) and ether (100 ml)
5. dry with materialThe organic phase was dried over magnesium sulphate
6. customthe solvent removed under reduced pressure
7. customThe resulting oil was triturated with cyclohexane (10 ml)
8. customthe resulting crystals (300 mg; unchanged starting material) removed by filtration
9. customThe mother liquors were evaporated under reduced pressure
10. customwas recrystallised from methanol/ethyl acetate

ORD record

ord-935000ca67bd4f85aaf8488519c84784

Source dataset

uspto-grants-1981_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04248876