(3S)-3-Methyl-4-(4-morpholinyl)-2,2-diphenyl-1-(1-pyrrolidinyl)-1-butanone is an intermediate in the synthesis of (S)-Moramide or Dextromoramide (M630190), which is a controlled substance (opiate). Analgesic (narcotic).
Definition
ChEBI: An N-acylpyrrolidine arising by formal condensation of pyrrolidine with (3S)-3-methyl-4-(morpholin-4-yl)-2,2-diphenylbutanoic acid. An opioid analgesic that is structurally related to methadone, it is more poweful than m
rphine but shorter acting. It has been used (particularly as the hydrogen tartrate salt) for the treatment of severe pain, but was discontinued in the UK in 2004.
Manufacturing Process
1 mol diphenylacetylpyrrolidine was added to a suspension of 1,1-1,3 mol
sodium oxide in 700 ml of toluene. The mixture was refluxed for a few hours
until the sodium compounds of the acetamide derivative were formed
completely. Then a slight excess of 1-(2-chloropropyl)morpholine was slowly
added, dissolved in an equal volume of toluene or xylene. This mixture was
refluxed for 6-8 hours. The reaction mixture was treated with water. The
organic layer was then extracted with dilute hydrochloric acid and this extract
was again made alkaline and extracted with ether. The extract was dried with
potassium carbonate. A small amount of diphenylacetylpyrrolidine crystallizes
from the ether. This is filtered off, petroleum ether is added and mixture is
placed in refrigerator. After some days the 1-(4-N-morpholino-4-methyl-2,2-
diphenylbutyryl)pyrrolidine is separated from this extract. M.P. 109-111°C.
Trademarks
Dimorlin Tartrate (SmithKline Beecham).
Therapeutic Function
Narcotic analgesic
dextromoramide Upstream-Materialien And Downstream Produkte
