Sodium Hydroxide → 1-[(10,11-dihydro-5H-dibenzo[a,d]-cyclohepten-5-yl)methyl]-4-piperidinone oxime
Reaction equation
[OH-:1].[Na+].[CH:3]1[C:13]2[CH2:12][CH2:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[CH:8]([CH2:18][N:19]3[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl.[NH2:27]O>C(O)C.O>[CH:3]1[C:13]2[CH2:12][CH2:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[CH:8]([CH2:18][N:19]3[CH2:24][CH2:23][C:22](=[N:27][OH:1])[CH2:21][CH2:20]3)[C:7]=2[CH:6]=[CH:5][CH:4]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
2.6 Parts of finely ground sodium hydroxide is added to a suspension of 3 parts of 1-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)methyl]-4-piperidinone and 1.5 part of hydroxylamine hydrochloride in 50 parts by volume of ethanol-water (4:1) solution. The resultant mixture is heated on a steam bath for about 5 hours and then partitioned between water and ethyl acetate. The aqueous layer is separated and extracted with a second portion of ethyl acetate. The ethyl acetate extracts are combined, dried, and concentrated to give 1-[(10,11-dihydro-5H-dibenzo[a,d]-cyclohepten-5-yl)methyl]-4-piperidinone oxime, as a white solid which melts at about 199°-202° C. after recrystallization from dioxane. This compound is represented by the following structural formula ##STR33##
Workup
- custompartitioned between water and ethyl acetate
- customThe aqueous layer is separated
- extractionextracted with a second portion of ethyl acetate
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f6f5f6b918784c2e8c719673ddeb769d
- Source dataset
- uspto-grants-1980_02
- Patent number
- US04188485
Reaction notes
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