HCID 13320299, compound → HCID 70454456, compound
Reaction equation
[I-].Cl[C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][C@H:7]1[C@@H:11]([OH:12])[CH2:10][N+:9](C)([CH2:13]C2C=CC=CC=2)[CH2:8]1>[Ag]=O.C(O)C>[CH3:13][N:9]1[CH2:8][C@H:7]([O:6][C:5]2[CH:21]=[CH:22][CH:23]=[CH:3][CH:4]=2)[C@H:11]([OH:12])[CH2:10]1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
A solution of 12.5 g. (28 mmoles) of cis-3-(3-chlorophenoxy)-4-hydroxy-1-methyl-1-phenylmethylpyrrolidinium iodide in 400 ml. of ethanol was stirred at 45° C. with 3.5 g. (15 mmoles) of silver oxide for 1 hr. The solids were removed by filtration and the filtrate was concentrated to 100 ml., treated with 0.5 g. of 10% palladium-on-charcoal catalyst and was shaken under hydrogen at 60° C. for 3 hr. The mixture was cooled and the catalyst was collected by filtration. The filtrate was concentrated and the residue was treated with dilute sodium hydroxide and extracted into methylene chloride. The solution was concentrated and redissolved in hot cyclohexane, treated with charcoal, separated by filtration through Celite and recrystallized from cyclohexane to give 4.6 g. (85%) of white needles (m.p. 78°-81° C.).
Workup
- customThe solids were removed by filtration
- concentrationthe filtrate was concentrated to 100 ml
- addition, treated with 0.5 g
- temperatureThe mixture was cooled
- filtrationthe catalyst was collected by filtration
- concentrationThe filtrate was concentrated
- additionthe residue was treated with dilute sodium hydroxide
- extractionextracted into methylene chloride
- concentrationThe solution was concentrated
- dissolutionredissolved in hot cyclohexane
- additiontreated with charcoal
- customseparated by filtration through Celite
- customrecrystallized from cyclohexane
- customto give 4.6 g
Sources & evidence
- ORD record
- ord-92c21442839c4d1abe07c91afb30d268
- Source dataset
- uspto-grants-1984_06
- Patent number
- US04452809
Reaction notes
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