u00d7 60 ml and then with ether 3 u00d7 60 ml the solid was air dried overnight to give 1 79 g of a white solid as the dihydrochloride salt mp 255 256 u00b0 c analysis calculated for c 32 h 42 cl 2 n 2 o c 70 97 h 7 82 n 5 17 found c 70 45 h 7 67 n 5 09 2 4 4 diphenylbutyl 1 2 3 4 tetrahydro isoquinolin 5 ol 2 44 g 6 83 mmol was dissolved in etoh 70 ml formaldehyde 37 0 536 ml 7 17 mmol and cyclohexylamine 0 820 ml 7 17 mmol were added and the reaction heated to 50 u00b0 c for 10 days the solvent was removed and the crude reaction chromatographed on silica gel eluting with etoac isolate 2 44 g 76 of product as an oil the oil 0 61 g 1 30 mmol was then dissolved in et 2 o 10 ml oxalic acid 0 33 g 2 62 mmol in etoh 1 ml was added to the ether solution and the reaction stirred at room temperature for 18 hours the light tan precipitate was filtered and washed with etoac and dried in vacuo over p 2 o 5 to give 0 61 g 73 of the oxalic acid salt mp 127 144 u00b0 c analysis calculated for c 32 h 40 n 2 o 1 84 c 2 h 2 o 4 c 67 56 h 6 94 n 4 42 found c 67 56 h 6 90 n 4 26 6 cyclohexylaminomethyl 2 4 4 diphenylbutyl 1 2 3 4 tetrahydro isoquinolin 5 ol 1 84 g 3 93 mmol was dissolved in meoh 35 ml formaldehyde 37 0 60 ml 8 0 mmol was added and.