1,2,3,4-tetrahydro-8-quinolinol -Drug Synthesis Database

【结构式】

【分子编号】16022

【品名】1,2,3,4-tetrahydro-8-quinolinol

【CA登记号】

【分子式】C₉H₁₁NO

【分子量】149.19248

【元素组成】C 72.46% H 7.43% N 9.39% O 10.72%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(I)

The acylation of 8-hydroxy-1,2,3,4-tetrahydroquinoline (I) with nicotinoyl chloride (II) by means of triethylamine in benzene gives 8-hydroxy-1-nicotinoyl-1,2,3,4-tetrahydroquinoline (III), which is condensed with epichlorohydrin (IV) by means of potassium tert-butoxide in DMF to yield 1-nicotinoyl-8-(2,3-epoxy-1-propoxy)-1,2,3,4-tetrahydroquinoline (V). Finally, this compound is condensed with isopropylamine (VI) in ethanol.

参考文献中间体

合成目标

【1】 Graewinger, O.; Raabe, T.; Beyerle, R.; Scholtholt, J.; Nitz, R.E.; 1-Acyl-8-(3-amino-2-hydroxypropoxy)-1,2,3,4-tetrahydroquinolines, compositions and use. DD 153368; DE 2934609; EP 0025864; JP 56034668; US 4335123 .
【2】 Castaner, J.; Serradell, M.N.; Hillier, K.; Nicainoprol. Drugs Fut 1984, 9, 10, 749.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	16022	1,2,3,4-tetrahydro-8-quinolinol		C₉H₁₁NO	详情	详情
(II)	10753	Nicotinoyl chloride		C₆H₄ClNO	详情	详情
(III)	34334	[8-hydroxy-3,4-dihydro-1(2H)-quinolinyl](3-pyridinyl)methanone		C₁₅H₁₄N₂O₂	详情	详情
(IV)	10146	Epichlorohydrin; 2-(Chloromethyl)oxirane	106-89-8	C₃H₅ClO	详情	详情
(V)	34335	[8-(2-oxiranylmethoxy)-3,4-dihydro-1(2H)-quinolinyl](3-pyridinyl)methanone		C₁₈H₁₈N₂O₃	详情	详情
(VI)	23933	2-Propanamine; Isopropylamine	75-31-0	C₃H₉N	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

The condensation of 4-benzyl-2-(chloromethyl)morpholine (I) with 8-hydroxy-1,2,3,4-tetrahydroquinoline (II) by means of NaH in hot DMF gives 8-(4-benzylmorpholin-2-ylmethoxy)-1,2,3,4-tetrahydroquinoline (III), which is methylated with methyl iodide and K2CO3 in refluxing acetone yielding the corresponding N-methyl derivative (IV). Finally, this compound is debenzylated by hydrogenolysis with H2 over Pd/C in ethanol.

参考文献中间体

合成目标

【1】 Tracy, M.; Ngo, J.; Castaner, J.; Dabelotine Mesylate. Drugs Fut 1996, 21, 9, 890.
【2】 Regnier, G.; Guillonneau, C.; Lepagnol, J. (ADIR et Cie.); Novel morpholine derivs., process for their preparation and pharmaceutical compsns. containing them. AU 8813520; EP 0286495; FR 2612926; JP 1988255279; US 4782054 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	13396	4-Benzyl-2-(chloromethyl)morpholine	C₁₂H₁₆ClNO	详情	详情
(II)	16022	1,2,3,4-tetrahydro-8-quinolinol	C₉H₁₁NO	详情	详情
(III)	16023	(4-benzyl-1,4-oxazinan-2-yl)methyl 1,2,3,4-tetrahydro-8-quinolinyl ether; 8-[(4-benzyl-1,4-oxazinan-2-yl)methoxy]-1,2,3,4-tetrahydroquinoline	C₂₁H₂₆N₂O₂	详情	详情
(IV)	16024	8-[(4-benzyl-1,4-oxazinan-2-yl)methoxy]-1-methyl-1,2,3,4-tetrahydroquinoline; (4-benzyl-1,4-oxazinan-2-yl)methyl 1-methyl-1,2,3,4-tetrahydro-8-quinolinyl ether	C₂₂H₂₈N₂O₂	详情	详情

Extended Information