1-Methyl-4-piperidone

1-Methyl-4-piperidone (also known as N-methyl-4-piperidone) is a clear dark yellow liquid organic compound with molecular formula C6H11NO. It is the N-methyl substituted variant of 4-piperidone. == Applications == 1-Methyl-4-piperidone is used as a building block for a variety of pharmaceuticals, including: AC-90179 Alcaftadine Anpirtoline Azanator [37855-92-8] Azatadine B777-81 Bamipine BI-2536 [755038-02-9] BRL-54443 [57477-39-1] Cycliramine (not actual patented script method but still eligible, are using the precursor as for CTDP-32476). Danitracen DDD-016 Diphenylpyraline Hepzidine HP-365 [59142-29-9] HT 3261 Ketotifen Latrepirdine, maritupirdine, and dorastine Lifibrate Loratadine Lortalamine Lu 20-089, Lu 21-018, Lu 21-120, Lu 22-135, Lu 24-003, Lu 24-004, Lu 33-083, Lu 21-131, Lu 24-001, Lu 24-014, Lu 24-015, Lu 24-016, Lu 22-117, Lu 24-013, Lu 21-037, Lu 23-149. Patent: LY-334370 Mebhydrolin Medipine (c.f. budipine and prodipine) ML352 [1649450-12-3] MPPP Naratriptan Paridocaine [7162-37-0] Picenadol Pimavanserin Pimethixene, clopipazan, Lu 14-089, Lu 12-312, and P 344 [63834-14-0]. Piperylone RL71 [1195795-93-7] SN-22 Thenalidine Tienocarbine Tubastatin A [1252003-15-8] TFA salt: [1239262-52-2] Enpiperate and parapenzolate Propiverine and pentapiperide [7009-54-3] UMB103 RS 86 [3576-73-6] VU6001221 [2002495-17-0] EA-3834, EA-3580, EA-3443, EA-3580, EA-3443, CAR-302,196, CAR-302,282, and CAR-302,668 Edoxaban == Synthesis == The first synthesis of 1-methyl-4-piperidone was reported by Samuel M. McElvain in 1948. The method involves double Michael reaction between methylamine and two equivalents of ethyl acrylate, a Dieckmann cyclization (i.e. intramolecular Claisen condensation), saponification and decarboxylation. Another synthesis uses methylamine, formaldehyde and the ethyl ester of acetonedicarboxylic acid. A third synthesis consists of the ring closing of 1,5-dichloro-3-pentanone with methylamine. == See also == 4-Piperidone, the parent compound == References ==