Formaldehyde → 3,7-Dibenzyl-3,7-diazabicyclo[3.3.1]nonan-9-one
Reaction equation
[CH2:1]([N:8]1[CH2:13]CC(=O)CC1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Se]1[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]1.[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH2:30]=O>CO.C(O)(=O)C>[CH2:22]([N:29]1[CH2:30][CH:19]2[C:18](=[O:21])[CH:17]([CH2:13][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:20]2)[CH2:16]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1Participants
Procedure
Reaction scheme C using 1-benzyl-4-piperidone (25) in a manner closely analogous to the previous reactions scheme A which used 4-selenanone as a reactant. As illustrated, the aryl amine (again benzylamine) and paraformaldehyde react in the presence of glacial acetic acid and methanol to produce the N,N'-dibenzyl-3,7-diazabicyclo[3.3.1]nonan-9-one (26). This diazabicyclo[3.3.1]nonan-9-one (26) is then converted to one of three derivatives by one of three separate reaction pathways. Using perchloric acid in benzene and 3 Å molecular sieve with methanol, the hydroperchlorate amine salt of the 9,9-dimethoxy derivative (27) is produced. The use of perchloric acid in an aqueous media produces the hydraperchlorate amine salt of the 9,9-dihydroxy derivative (28). And, in a manner analogous to the reaction scheme A, a sequential reduction using hydrazine hydrate in triethylene glycol and potassium hydroxide followed by perchloric acid in benzene produces the hydroperchlorate tertiary amine salt of the reduced form of the diazabicyclo[3.3.1]nonane (29). ##STR16##
Workup
- customReaction scheme C
Sources & evidence
- ORD record
- ord-5d7352d5773a429eab3e5afc7fe55b4d
- Source dataset
- uspto-grants-1991_08
- Patent number
- US05043445
Reaction notes
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