HCID 14553019, compound → HCID 23322817, compound
Reaction equation
[BrH:1].[Cl:2][C:3]1([C:11]([O:13][CH3:14])=[O:12])[CH2:10][CH:7]2[CH:8]=[CH:9][CH:4]1[NH:5][CH2:6]2>[Pd].CO>[BrH:1].[Cl:2][C:3]1([C:11]([O:13][CH3:14])=[O:12])[CH:4]2[CH2:9][CH2:8][CH:7]([CH2:6][NH:5]2)[CH2:10]1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
8.5 g. (0.03 moles) of 7-chloro-7-methoxycarbonyl-2-azabicyclo[2.2.2]oct-5-ene hydrobromide are dissolved in 85 ml. of methanol. 0.85 g. of a 10% palladium-on-charcoal catalyst are prehydrogenated in 15 ml. of methanol, and a clear solution of the starting material to be hydrogenated is added in a closed system. Hydrogenation is carried out in a closed system, the progress of the reaction is monitored by measuring the hydrogen consumption. When the calculated amount of hydrogen is used up, the reaction is terminated. When the reaction is not terminated timely, the reaction proceeds further and the chlorine is replaced by hydrogen. The catalyst is filtered off, the solution is evaporated. A crystalline material is obtained, which is triturated in about 20 ml. of acetone, and allowed to stand overnight in a refrigerator. The precipitate is filtered off on the next day, pulpified with two 5-ml. portions of cold acetone, and dried.
Workup
- customthe hydrogen consumption
- customthe reaction is terminated
- customWhen the reaction is not terminated timely
- filtrationThe catalyst is filtered off
- customthe solution is evaporated
- customA crystalline material is obtained
- customwhich is triturated in about 20 ml
- filtrationThe precipitate is filtered off on the next day
- dry with materialportions of cold acetone, and dried
Sources & evidence
- ORD record
- ord-16bc73f66f6b4360ba54674dafccb44d
- Source dataset
- uspto-grants-1986_01
- Patent number
- US04563464
Reaction notes
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