Oxalic acid--4-(1-benzylpiperidin-3-yl)-1,2-phenylene diacetate (1/1) → Oxalic acid--4-(piperidin-3-yl)-1,2-phenylene diacetate (1/1)
Reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].C([N:14]1[CH2:19][CH2:18][CH2:17][CH:16]([C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27](=[O:29])[CH3:28])=[C:22]([O:30][C:31](=[O:33])[CH3:32])[CH:21]=2)[CH2:15]1)C1C=CC=CC=1>C(O)C.[H][H]>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[C:31]([O:30][C:22]1[CH:21]=[C:20]([CH:16]2[CH2:17][CH2:18][CH2:19][NH:14][CH2:15]2)[CH:25]=[CH:24][C:23]=1[O:26][C:27](=[O:29])[CH3:28])(=[O:33])[CH3:32]Participants
4
Procedure
5 g of 10% palladized activated carbon were added to a solution of 10 g of the product of Step C in 600 ml of ethanol and hydrogen was introduced until hydrogen absorption ceased. The mixture was filtered and the filtrate was evaporated to dryness. The residue was dissolved in ethanol and the solution was cooled and vacuum filtered. The mother liquors were concentrated while progressively adding ethanol to a volume of 50 ml and was cooled and vacuum filtered. The recovered crystals were dried to obtain 3.25 g of 3-(3',4'-diacetoxyphenyl)-piperidine oxalate melting at 160° C.
Workup
- filtrationThe mixture was filtered
- customthe filtrate was evaporated to dryness
- dissolutionThe residue was dissolved in ethanol
- temperaturethe solution was cooled
- filtrationvacuum filtered
- concentrationThe mother liquors were concentrated while progressively adding ethanol to a volume of 50 ml
- temperaturewas cooled
- filtrationvacuum filtered
- customThe recovered crystals were dried
Sources & evidence
- ORD record
- ord-b6de42f5ef29400aa1df73ae31ade5a8
- Source dataset
- uspto-grants-1977_09
- Patent number
- US04046901
Reaction notes
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