Phenethylamine → Benzylmethyl(tetrahydropyran-4-yl)amine
Reaction equation
[CH2:1]([CH2:8][NH2:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(Cl)Cl.[CH3:14][OH:15]>>[CH2:1]([CH2:8][NH:9][CH:1]1[CH2:2][CH2:3][O:15][CH2:14][CH2:8]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
3
Procedure
Into a similar device to that used in Example 7 were charged 1.38 g (5.0 mmol) of tetrahydropyranyl-4-p-toluenesulfonate synthesized in Example 6 and having a purity of 93% and 3.18 g (26.0 mmol) of benzylmethylamine, and the mixture was reacted at 70° C. for 4 hours and further at 90° C. for 5 hours. After completion of the reaction, the resulting reaction mixture was concentrated under reduced pressure and purified by silica gel column chromatography (Filler: Wako gel C-200 (available from Wako Junyaku Co.), Eluent: chloroform/methanol (=9/1 (volume ratio)) to obtain 0.72 g (yield: 70%) of 4-benzylmethylaminotetrahydropyrane having a purity of 90% (areal percentage according to high performance liquid chromatography) as a pale yellowish liquid.
Workup
- custom