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ChemicalBook CAS DataBase List N,alpha-dimethylcyclohexaneethylamine
101-40-6

N,alpha-dimethylcyclohexaneethylamine synthesis

6synthesis methods
-

Yield:101-40-6 91.3%

Reaction Conditions:

with sodium hydroxide in water;toluene

Steps:

3
EXAMPLE 3.; )032] To a 100 ml 3-neck flask fitted with a mechanical stirrer, a condenser, a thermocouple, and a nitrogen purge stream was added 1.9468 g (0.01254 mole) of propylhexedrine, 2.65 g toluene, and 0.79 g (0.00624 mole) of benzyl chloride. The reactor was continuously purged with nitrogen. The reaction mass was heated to 1210C for 4.75 hr. A slurry of a crystalline solid in an oil formed. To this was added 4.60 g of toluene and 7.32 g of water. The mixture was vigorously stirred and heated to 5O0C for 10 minutes. The solids completely dissolved. After cooling, the two liquid phases were transferred to a separatory funnel. Water, (0.85 g) and a 1.62 g amount of toluene were used to rinse the residues in the flask into the separatory funnel. The layers were separated into a 9.10 g lower water layer containing the propylhexedrine hydrochloride and an 8.19 g upper organic layer containing the N-benzylpropylhexedrine. HPLC analysis of the organic layer found 20.76%, by weight, of benzylpropylhexedrine base which is 1.70 g (0.00692 mole) which is a 110% yield. The propylhexedrine hydrochloride in the water layer was converted to the base by adding 5.68 g of toluene and 1.18 g of 25% sodium hydroxide. The mixture was aggressively shaken. The layers were separated into a 9.05 g water layer having a pH of 13 and a 6.79 g toluene layer. The toluene layer was analyzed by gas chromatography and found to contain 13.10%, by weight, propylhexedrine base which is equivalent to 0.8895 g (0.00572 mole) or a 91.3% yield.

References:

MALLINCKRODT INC. WO2006/73547, 2006, A1 Location in patent:Page/Page column 8

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