4303. Furethidine

Nomenclature

CAS number: 2385-81-1
4-Phenyl-1-[2-[(tetrahydro-2-furanyl)methoxy]ethyl]-4-piperidinecarboxylic acid ethyl ester; 4-phenyl-1-[2-(tetrahydrofurfuryloxy)ethyl]isonipecotic acid ethyl ester; ethyl 1-(tetrahydrofurfuryloxyethyl)-4-phenylpiperidine-4-carboxylate; 1-(2′-tetrahydrofurfuryloxyethyl)norpethidine.
C21H31NO4; mol wt 361.48.
C 69.78%, H 8.64%, N 3.87%, O 17.70%.

Description and references

Prepn: Frearson, Stern, GB 797448 (1958 to J. F. Macfarlan & Co.); Frearson et al., J. Chem. Soc. 1960, 2103.

Chemical structure

Properties

bp0.5 210°; bp0.3 175-183°. mp ≈28°. nD20 1.5219. pKa 7.48.

Derivative

Methiodide.
C22H34INO4; mol wt 503.41.
C 52.49%, H 6.81%, I 25.21%, N 2.78%, O 12.71%.

Properties

Crystals from ethyl acetate, mp 174°.

Note

This is a controlled substance (opiate): 21 CFR, 1308.11.