Synthesis of amine derivatives
AssigneeSumitomo Chemical Company, Limited
InventorsFujio Masuko, Tadashi Katsura
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AssigneeSumitomo Chemical Company, Limited
InventorsFujio Masuko, Tadashi Katsura
Estimating the term…
An amine of the formula, ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are each hydrogen, alkyl or the like and n is 1, 2 or 3, including .alpha.-phenyl-.beta.-(p-tolyl)-ethylamine, which is useful as an optically resolving agent, an intermediate of medicines and the like, is effectively produced by a novel process comprising hydrolysis of the corresponding nitrile of the formula, ##STR2## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and n are the same as above, followed by alkali-decomposition of the resulting amide of the formula, ##STR3## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and n are the same as above. An amide including the above one is effectively produced by hydrolysis of the corresponding nitrile in the presence of a base and hydrogen peroxide using an organic quaternary ammonium salt and/or a tertiary amine as a catalyst.
A process for preparing an amine derivative of the formula (1), ##STR15## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are independently hydrogen atom, a halogen atom, a hydroxy, trihalogenomethyl, phenyl, phenoxy or phenylthio group, or a straight or branched C.sub.1 -C.sub.6 alkyl, alkenyl, alkoxyl, alkylthio, dialkylamino or alkylsulfonyl group, n is an integer of 1 to 3, provided that R.sub.3 s may be the same or different when n is 2 or 3, and either R.sub.1 and R.sub.2 or R.sub.4 and R.sub.5 may be bonded through the same or different atom, which comprises condensing an acetonitrile compound of the formula (4), ##STR16## wherein R.sub.4 and R.sub.5 are as defined above, with a halide compound of the formula (5), ##STR17## wherein R.sub.1, R.sub.2, R.sub.3 and n are as defined above and X is a halogen atom, in the presence of a base to produce a nitrile compound of the formula (3), ##STR18## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and n are as defined above, hydrolyzing said compound of the formula (3) using as a catalyst an organic quaternary ammonium salt and/or tertiary amine in the presence of a base and hydrogen peroxide to produce an amide compound of the formula (2), ##STR19## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and n are as defined above, and contacting said amide compound of the formula (2) with a halogen, an alkali metal hypohalite or an alkaline earth metal hypohalite in the presence of a base.
A process for preparing an amide derivative represented by the general formula (I),
Dependencies are inferred from the claim text.