Diphenylmethane → 1-Benzhydryl-3-[3-(trifluoromethyl)phenoxy]azetidine
Reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[O:6][CH:7]1[CH2:10][NH:9][CH2:8]1.[C:16]1([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CO>[C:16]1([CH:22]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:9]2[CH2:10][CH:7]([O:6][C:5]3[CH:11]=[CH:12][CH:13]=[C:3]([C:2]([F:1])([F:14])[F:15])[CH:4]=3)[CH2:8]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A 30 gallon glass-lined reactor was charged with a solution containing equal parts of 3-(3-trifluoromethylphenoxy)azetidine and diphenylmethane in methanol as obtained from the catalytic hydrogenolysis of 78.32 moles of 1-diphenylmethyl-3-(3-trifluoromethylphenoxy)azetidine. The methanol was distilled off at a pressure of 150 mm Hg until the reactor temperature reached 65° C. The reactor was flushed with nitrogen and charged with 117.4 moles of urea. Heating was continued to approximately 135° C. and held at 135° C. until thin layer chromatographic analysis showed the azetidine derivative to be consumed. When the reaction was complete the mixture was cooled to approximately 80° C. A 30 gallon receiver equipped with an agitator was charged with 80 L of petroleum ether (80°-110° C. boiling range) and the contents of the reactor drained into the receiver with the agitator at high speed. The mixture was slowly cooled to 50° C. and held at that temperature for 5-6 hours. The resulting slurry was then pumped onto a vacuum filter and the filter cake compressed under a rubber dam for 4-5 hours to remove as much solvent as possible.
Workup
- additionA 30 gallon glass-lined reactor was charged with a solution
Sources & evidence
- ORD record
- ord-b0c44b147be34edca9f081a624e46c40
- Source dataset
- uspto-grants-1993_02
- Patent number
- US05183903
Reaction notes
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