Page 240 - Chemical and process design handbook

Speight_Part II_C 11/7/01 3:08 PM Page 2.180

CODEINE

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Codeine (boiling point: 250 C at 22 mmHg, melting point: 157 C, density:
1.32) can be isolated from opium and morphine (also obtained from
opium). To direct this alkylation to the phenolic hydroxyl and to reduce
alkylation of the tertiary nitrogen, a quaternary nitrogen-alkylating agent,
phenyltrimethylammonium hydroxide, is employed. This results in yields
of 90 to 93 percent codeine and some recovery of unalkylated morphine.
The alkylation is carried out with the morphine dissolved in absolute alco-
hol in the presence of potassium ethylate. The dimethyl aniline and solvents
are recovered and reused.

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