【药物名称】Alifedrine hydrochloride, D-13625
化学结构式(Chemical Structure):
参考文献No.61895
标题:Alifedrine
作者:B鋒re, M.; Thiemer, K.; Engel, J.; Breuel, H.P.; Stroman, F.; Kleemann, A.
来源:Drugs Fut 1984,9(10),727
合成路线图解说明:

Mannich reaction of acetylcyclohexane (V), paraformaldehyde and 1-norephedrine (I) in the presence of hydrochloric acid yields alifedrine hydrochloride. Mannich reaction of 1-acetylcyclohexene (VI) with paraformaldehyde and (I) followed by catalytic hydrogenation of the resulting beta-aminoketone (III) also gives alifedrine hydrochloride.

合成路线图解说明:

For [14C]-labelling of alifedrine, the following reaction sequence has been used: In the first step Friedel-Crafts'-like acylation of ethylene (A) with cyclohexanoyl chloride (VII) in the presence of aluminum chloride yields beta-chloroethylcyclohexyl ketone (VIII), which reacts with (I) to give alifedrine hydrochloride. Alifedrine has also been synthesized by catalytic hydrogenation of (V) with 1-norephedrine (I) in the presence of hydrochloric acid and paraformaldehyde.

合成路线图解说明:

Alifedrine hydrochloride can be synthesized by condensation of acetylcyclohexane with the bisoxazolidine (IV), which is obtained by reaction of (I) with paraformaldehyde in aqueous solution. Finally, alifedrine can be obtained by condensation of 3-oxo-3-cyclohexylpropanal (X) and norephedrine (I) under reducing conditions (VI).

参考文献No.604476
标题:Syntheses of 14C-1-erythro-norephedrine and its N-substitution products 14C-oxyfedrine and 14C-D 13,625
作者:Klingler, K.G.; Engel, J.; Bickel, E.
来源:Arzneim-Forsch Drug Res 1983,33(9),1213
合成路线图解说明:

For [14C]-labelling of alifedrine, the following reaction sequence has been used: In the first step Friedel-Crafts'-like acylation of ethylene (A) with cyclohexanoyl chloride (VII) in the presence of aluminum chloride yields beta-chloroethylcyclohexyl ketone (VIII), which reacts with (I) to give alifedrine hydrochloride. Alifedrine has also been synthesized by catalytic hydrogenation of (V) with 1-norephedrine (I) in the presence of hydrochloric acid and paraformaldehyde.

参考文献No.701199
标题:Novel cycloaliphatic enamines
作者:Engel, J.; et al.
来源:DE 3213371
合成路线图解说明:

For [14C]-labelling of alifedrine, the following reaction sequence has been used: In the first step Friedel-Crafts'-like acylation of ethylene (A) with cyclohexanoyl chloride (VII) in the presence of aluminum chloride yields beta-chloroethylcyclohexyl ketone (VIII), which reacts with (I) to give alifedrine hydrochloride. Alifedrine has also been synthesized by catalytic hydrogenation of (V) with 1-norephedrine (I) in the presence of hydrochloric acid and paraformaldehyde.

参考文献No.701205
标题:Cycloaliphatic ketoamines
作者:Engel, J.; et al.
来源:DE 2919495; FR 2426040; GB 2023575; JP 54151950; US 4542159
合成路线图解说明:

Mannich reaction of acetylcyclohexane (V), paraformaldehyde and 1-norephedrine (I) in the presence of hydrochloric acid yields alifedrine hydrochloride. Mannich reaction of 1-acetylcyclohexene (VI) with paraformaldehyde and (I) followed by catalytic hydrogenation of the resulting beta-aminoketone (III) also gives alifedrine hydrochloride.

合成路线图解说明:

For [14C]-labelling of alifedrine, the following reaction sequence has been used: In the first step Friedel-Crafts'-like acylation of ethylene (A) with cyclohexanoyl chloride (VII) in the presence of aluminum chloride yields beta-chloroethylcyclohexyl ketone (VIII), which reacts with (I) to give alifedrine hydrochloride. Alifedrine has also been synthesized by catalytic hydrogenation of (V) with 1-norephedrine (I) in the presence of hydrochloric acid and paraformaldehyde.

参考文献No.701206
标题:
作者:Tr鰉er, H.G.; Sheldrick, W.S.; Engel, J.
来源:Chem Ztg 1982,106(Suppl. 1),427
合成路线图解说明:

Alifedrine hydrochloride can be synthesized by condensation of acetylcyclohexane with the bisoxazolidine (IV), which is obtained by reaction of (I) with paraformaldehyde in aqueous solution. Finally, alifedrine can be obtained by condensation of 3-oxo-3-cyclohexylpropanal (X) and norephedrine (I) under reducing conditions (VI).

参考文献No.701207
标题:Cycloaliphatic ketoamines
作者:Engel, J.; et al.
来源:DE 3043350
合成路线图解说明:

Alifedrine hydrochloride can be synthesized by condensation of acetylcyclohexane with the bisoxazolidine (IV), which is obtained by reaction of (I) with paraformaldehyde in aqueous solution. Finally, alifedrine can be obtained by condensation of 3-oxo-3-cyclohexylpropanal (X) and norephedrine (I) under reducing conditions (VI).

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