2-chloro-N-cyclohexylacetamide -Drug Synthesis Database

【结构式】

【分子编号】27377

【品名】2-chloro-N-cyclohexylacetamide

【CA登记号】

【分子式】C₈H₁₄ClNO

【分子量】175.658

【元素组成】C 54.7% H 8.03% Cl 20.18% N 7.97% O 9.11%

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：(III)

The reaction of cyclohexylamine (I) with chloroacetyl chloride (II) in water in the presence of sodium hydroxide gives N-cyclohexyl-2-chloro-acetamide (III), which by reaction with piperazine (IV) in water is converted to N-[(N-cyclohexylcarbamoyl)methyl]piperazine (V). This compound is then treated with one equivalent of HCl.

参考文献中间体

合成目标

【1】 Corvi-Mora, C. (Camillo Corvi SpA); N-Cyclohexyl-piperazino acetamides and propionamides. US 4123530; US 4278796 .
【2】 de Angelis, L.; Esaprazole hydrochloride. Drugs Fut 1986, 11, 4, 263.

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)	17966	cyclohexanamine; cyclohexyl amine; cyclohexylamine	108-91-8	C₆H₁₃N	详情	详情
(II)	11296	2-Chloroacetyl chloride; Chloroacetic chloride	79-04-9	C₂H₂Cl₂O	详情	详情
(III)	27377	2-chloro-N-cyclohexylacetamide		C₈H₁₄ClNO	详情	详情
(IV)	10355	Diethylenediamine; Piperazine	110-85-0	C₄H₁₀N₂	详情	详情
(V)	27378	N-cyclohexyl-2-(1-piperazinyl)acetamide		C₁₂H₂₃N₃O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IX)

Acylation of 4-piperidone ethylene ketal (I) with 3-chloro-4-fluorobenzoyl chloride (II) in the presence of Et3N gave amide (III). After ketal hydrolysis of (III) using 80% formic acid and CuSO4, treatment of the resulting N-acyl piperidone (IV) with dimethyloxosulfonium methylide provided epoxide (V). Subsequent ring opening of (V) with HF-pyridine complex afforded the fluoro alcohol (VI), which was converted to tosylate (VII). Then, Gabriel synthesis via the corresponding phthalimide (VIII) produced amine (IX). The title compound was then obtained by condensation of 6-(2-furanyl)pyridine-2-carboxaldehyde (X) with amine (IX), followed by reduction of the intermediate imine with KBH4 in MeOH.

参考文献中间体

合成目标

【1】 Koek, W.; Cosi, C.; Jubault, N.; Funes, P.; Assié, M.-B.; Vacher, B.; Kleven, M.; Bonnaud, B.; Novel derivatives of 2-pyridinemethylamine as selective, potent, and orally active agonists at 5-HT1A receptors. J Med Chem 1999, 42, 9, 1648.

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)	11338	1,4-Dioxa-8-azaspiro[4.5]decane; 4-Piperidone ethylene ketal	177-11-7	C₇H₁₃NO₂	详情	详情
(II)	24370	3-chloro-4-fluorobenzoyl chloride	65055-17-6	C₇H₃Cl₂FO	详情	详情
(III)	24371	(3-chloro-4-fluorophenyl)(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)methanone		C₁₄H₁₅ClFNO₃	详情	详情
(IV)	24372	1-(3-chloro-4-fluorobenzoyl)-4-piperidinone		C₁₂H₁₁ClFNO₂	详情	详情
(V)	24373	(3-chloro-4-fluorophenyl)(1-oxa-6-azaspiro[2.5]oct-6-yl)methanone		C₁₃H₁₃ClFNO₂	详情	详情
(VI)	24374	(3-chloro-4-fluorophenyl)[4-fluoro-4-(hydroxymethyl)-1-piperidinyl]methanone		C₁₃H₁₄ClF₂NO₂	详情	详情
(VII)	24375	[1-(3-chloro-4-fluorobenzoyl)-4-fluoro-4-piperidinyl]methyl 4-methylbenzenesulfonate		C₂₀H₂₀ClF₂NO₄S	详情	详情
(VIII)	24376	2-[[1-(3-chloro-4-fluorobenzoyl)-4-fluoro-4-piperidinyl]methyl]-1H-isoindole-1,3(2H)-dione		C₂₁H₁₇ClF₂N₂O₃	详情	详情
(IX)	27377	2-chloro-N-cyclohexylacetamide		C₈H₁₄ClNO	详情	详情
(X)	24382	6-(2-furyl)-2-pyridinecarbaldehyde		C₁₀H₇NO₂	详情	详情

Extended Information