1-heptanamine; heptylamine -Drug Synthesis Database

【结构式】

【分子编号】23252

【品名】1-heptanamine; heptylamine

【CA登记号】111-68-2

【分子式】C₇H₁₇N

【分子量】115.21872

【元素组成】C 72.97% H 14.87% N 12.16%

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：(B)

The reaction of p-chlorobenzaldehyde (I) sodium cyanide and ethyl acetate gives ethyl 4-(p-chlorophenyl)-4-oxobutyrate (II), which is hydrolyzed with KOH to the corresponding free acid (III). The reduction of (III) with Zn and aqueous HCl affords 4-(p-chlorophenyl)butyric acid (IV), which is condensed with heptylamine (B) by means of oxalyl chloride (A) in refluxing benzene to yield N-heptyl-4-(p-chlorophenyl)butyramide (V), which is reduced with diborane in refluxing THF to afford N-heptyl-4-(p-chlorophenyl)butylamine (VI). The acetylation of (VI) with acetyl chloride (C) by means of Na2CO3 in acetone gives N-acetyl-N-heptyl-4-(p-chlorophenyl)butylamine (VII), which is reduced with diborane as before to yield N-ethyl-N-heptyl-4-(p-chlorophenyl)butylamine (VIII). The quaternization of (VIII) with refluxing ethyl bromide (D) gives N,N-diethyl-N-heptyl-4-(p-chlorophenyl)butylammonium bromide (IX), which by elution through a column with Dowex 1-X8, hydroxide form, resin is converted into N,N-diethyl-N-heptyl-4-(p-chlorophenyl)butyl ammonium hydroxide (X). Finally, this compound is salified with diluted aqueous phosphoric acid.

参考文献中间体

合成目标

【1】 Molloy, B.B.; Steinberg, M.I.; EP 0002604 .
【2】 Hillier, K.; Castaner, J.; Clofilium Phosphate. Drugs Fut 1981, 6, 12, 764.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(B)	23252	1-heptanamine; heptylamine	111-68-2	C₇H₁₇N	详情	详情
(A)	29841	Oxalyl chloride; 2-Chloro-2-oxoacetyl chloride	79-37-8	C₂Cl₂O₂	详情	详情
(D)	30344	1-bromoethane；ethyl bromide	74-96-4	C₂H₅Br	详情	详情
(I)	29029	4-chlorobenzaldehyde	104-88-1	C₇H₅ClO	详情	详情
(II)	37460	ethyl 4-(4-chlorophenyl)-4-oxobutanoate		C₁₂H₁₃ClO₃	详情	详情
(III)	37461	4-(4-chlorophenyl)-4-oxobutyric acid	3984-34-7	C₁₀H₉ClO₃	详情	详情
(IV)	37462	4-(4-chlorophenyl)butyric acid		C₁₀H₁₁ClO₂	详情	详情
(V)	37463	4-(4-chlorophenyl)-N-heptylbutanamide		C₁₇H₂₆ClNO	详情	详情
(VI)	37464	N-[4-(4-chlorophenyl)butyl]-1-heptanamine; N-[4-(4-chlorophenyl)butyl]-N-heptylamine		C₁₇H₂₈ClN	详情	详情
(VII)	37465	N-[4-(4-chlorophenyl)butyl]-N-heptylacetamide		C₁₉H₃₀ClNO	详情	详情
(VIII)	37466	N-[4-(4-chlorophenyl)butyl]-N-ethyl-N-heptylamine; N-[4-(4-chlorophenyl)butyl]-N-ethyl-1-heptanamine		C₁₉H₃₂ClN	详情	详情
(IX)	37467	N-[4-(4-chlorophenyl)butyl]-N,N-diethyl-1-heptanaminium bromide		C₂₁H₃₇BrClN	详情	详情
(X)	37468	N-[4-(4-chlorophenyl)butyl]-N,N-diethyl-1-heptanaminium hydroxide		C₂₁H₃₈ClNO	详情	详情
(C)	19273	acetyl chloride	75-36-5	C₂H₃ClO	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

The reaction of 4-neopentylbenzoic acid (I) with SOCl2 in refluxing dichloromethane gives the corresponding acid chloride (II) , which is condensed with heptylamine (III) in dichloromethane to yield 4-neopentyl-N-heptylbenzamide (IV). The reduction of (IV) with di(2-methoxyethoxy)sodium aluminum hydride in refluxing toluene affords 4-neopentyl-N-heptylbenzylamine (V), which is finally condensed with 2,4-difluorophenyl isocyanate (VI) in hexane. Compound (II) can also be obtained from neopentylbenzene (VII) and oxalyl chloride in the presence of aluminum chloride.

参考文献中间体

合成目标

【1】 Schaffer, S.A.; Dutia, M.D.; Largis, E.E.; Katocs, A.S. Jr.; Bloom, J.D.; Wang, C.-H.; De Vries, V.G.; Potential antiatherosclerotic agents. 5. And acyl-. J Med Chem 1986, 29, 1131.
【2】 De Vries, V.G. (American Cyanamid Co.); Antiatherosclerotic ureas and thioureas. BE 0900178; FR 2549473; GB 2149394; US 4623662 .
【3】 Castaner, J.; Prous, J.; CL-277082. Drugs Fut 1987, 12, 6, 527.

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)	23250	4-neopentylbenzoic acid		C₁₂H₁₆O₂	详情	详情
(II)	23251	4-neopentylbenzoyl chloride		C₁₂H₁₅ClO	详情	详情
(III)	23252	1-heptanamine; heptylamine	111-68-2	C₇H₁₇N	详情	详情
(IV)	23253	N-heptyl-4-neopentylbenzamide		C₁₉H₃₁NO	详情	详情
(V)	23254	N-(4-neopentylbenzyl)-1-heptanamine; N-heptyl-N-(4-neopentylbenzyl)amine		C₁₉H₃₃N	详情	详情
(VI)	23255	2,4-difluorophenyl isocyanate; 2,4-difluoro-1-isocyanatobenzene	59025-55-7	C₇H₃F₂NO	详情	详情
(VII)	28162	1-neopentylbenzene	1007-26-7	C₁₁H₁₆	详情	详情

Extended Information