2-chloro-N-(2,6-dimethylphenyl)acetamide -Drug Synthesis Database

【结构式】

【分子编号】24100

【品名】2-chloro-N-(2,6-dimethylphenyl)acetamide

【CA登记号】2198-53-0

【分子式】C₁₀H₁₂ClNO

【分子量】197.66412

【元素组成】C 60.76% H 6.12% Cl 17.94% N 7.09% O 8.09%

与该中间体有关的原料药合成路线共 6 条

合成路线1 合成路线2 合成路线3 合成路线4 合成路线5 合成路线6

合成路线1

该中间体在本合成路线中的序号：(III)

1) The acylation of 2,6-dimethylaniline (II) with chloroacetyl chloride by means of triethylamine in dichloromethane gives N-(2,6-dimethylphenyl) chloroacetamide (III), which is condensed with piperidine (IV) in refluxing ethanol to yield N-(2,6-dimethylphenyl)-2-piperazinoacetamide IV). Finally, this compound is condensed with 3-(2-methoxyphenoxy)-12-epoxypropane (VI) in refluxing methanol toluene.

参考文献中间体

合成目标

【1】 Ainsworth, A.T.; Smith, D.G. (SmithKline Beecham plc); Ethanamine derivs., their preparation and use in pharmaceutical compsns. EP 0023385 .
【2】 Prous, J.; Castaner, J.; RANOLAZINE < Rec INN; USAN >. Drugs Fut 1988, 13, 9, 837.

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)	11296	2-Chloroacetyl chloride; Chloroacetic chloride	79-04-9	C₂H₂Cl₂O	详情	详情
(II)	17527	2,6-Xylidine; 2,6-Dimethylaniline; 2,6-Dimethylphenylamine	87-62-7	C₈H₁₁N	详情	详情
(III)	24100	2-chloro-N-(2,6-dimethylphenyl)acetamide	2198-53-0	C₁₀H₁₂ClNO	详情	详情
(IV)	10355	Diethylenediamine; Piperazine	110-85-0	C₄H₁₀N₂	详情	详情
(V)	24102	N-(2,6-dimethylphenyl)-2-(1-piperazinyl)acetamide		C₁₄H₂₁N₃O	详情	详情
(VI)	24103	2-[(2-methoxyphenoxy)methyl]oxirane		C₁₀H₁₂O₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

2) The condensation of epoxide (VI) with piperazine (IV) in refluxing isopropanol gives 1-[3-(2-methoxyphenoxy)-2-hydroxypropyl]piperazine (VII), which is then condensed with chloroacetamide (III) in refluxing ethanol.

参考文献中间体

合成目标

【1】 Ainsworth, A.T.; Smith, D.G. (SmithKline Beecham plc); Ethanamine derivs., their preparation and use in pharmaceutical compsns. EP 0023385 .
【2】 Prous, J.; Castaner, J.; RANOLAZINE < Rec INN; USAN >. Drugs Fut 1988, 13, 9, 837.

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)	11296	2-Chloroacetyl chloride; Chloroacetic chloride	79-04-9	C₂H₂Cl₂O	详情	详情
(II)	17527	2,6-Xylidine; 2,6-Dimethylaniline; 2,6-Dimethylphenylamine	87-62-7	C₈H₁₁N	详情	详情
(III)	24100	2-chloro-N-(2,6-dimethylphenyl)acetamide	2198-53-0	C₁₀H₁₂ClNO	详情	详情
(IV)	10355	Diethylenediamine; Piperazine	110-85-0	C₄H₁₀N₂	详情	详情
(VI)	24103	2-[(2-methoxyphenoxy)methyl]oxirane		C₁₀H₁₂O₃	详情	详情
(VII)	24109	1-(2-methoxyphenoxy)-3-(1-piperazinyl)-2-propanol		C₁₄H₂₂N₂O₃	详情	详情

合成路线3

该中间体在本合成路线中的序号：(III)

Compound can be prepared in two related ways: 1) The acylation of 2,6-dimethylaniline (I) with chloroacetyl chloride (II) in acetic acid gives omega-chloro-2,6-dimethylacetanilide (III), which is then condensed with disodium salt of iminodiacetic acid (IV) in refluxing ethanol-water. 2) The reaction of (III) with ammonia in ethanol gives omega-amino-2,6-dimethylacetanilide (V), which is finally treated with chloroacetic acid (A) and NaOH in refluxing 95% ethanol.

参考文献中间体

合成目标

【1】 Castaner, J.; Blancafort, P.; Serradell, M.N.; Paton, D.M.; Lidofenin. Drugs Fut 1979, 4, 5, 342.
【2】 Callery, P.S.; et al.; Tissue distribution of technetium-99m and carbon-14 labeled N-(2,6-dimethylphenylcarbamoylmethyl)iminodiacetic acid. J Med Chem 1976, 19, 7, 962-964.

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)	11847	2-Chloroacetic acid; Chloroacetic Acid	79-11-8	C₂H₃ClO₂	详情	详情
(I)	17527	2,6-Xylidine; 2,6-Dimethylaniline; 2,6-Dimethylphenylamine	87-62-7	C₈H₁₁N	详情	详情
(II)	11296	2-Chloroacetyl chloride; Chloroacetic chloride	79-04-9	C₂H₂Cl₂O	详情	详情
(III)	24100	2-chloro-N-(2,6-dimethylphenyl)acetamide	2198-53-0	C₁₀H₁₂ClNO	详情	详情
(IV)	39492	2-[(carboxymethyl)amino]acetic acid	142-73-4	C₄H₇NO₄	详情	详情
(V)	39493	2-amino-N-(2,6-dimethylphenyl)acetamide		C₁₀H₁₄N₂O	详情	详情

合成路线4

该中间体在本合成路线中的序号：(IV)

参考文献中间体

合成目标

【1】 Deshpande PB, Chauhan AJ. 2006. Crystalline and amorphous form of ranolazine and the process for manufacturing them. WO 2006008753

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)	10355	Diethylenediamine; Piperazine	110-85-0	C₄H₁₀N₂	详情	详情
(II)	24103	2-[(2-methoxyphenoxy)methyl]oxirane		C₁₀H₁₂O₃	详情	详情
(III)	24109	1-(2-methoxyphenoxy)-3-(1-piperazinyl)-2-propanol		C₁₄H₂₂N₂O₃	详情	详情
(IV)	24100	2-chloro-N-(2,6-dimethylphenyl)acetamide	2198-53-0	C₁₀H₁₂ClNO	详情	详情

合成路线5

该中间体在本合成路线中的序号：(V)

参考文献中间体

合成目标

【1】 Li SC, Huang HQ, Li ZJ. 2003. Synthesis of a novel antianginal agent Ranolazine. 中国药物化学杂志，13: 283～285
【2】 Lu WC, Li YQ, Zhao XG, et aL. 2004. Synthesis of ranolazine中国医药工业杂志，35: 641～642
【3】 Wang LS, Feng XY, Zhu HY. 2003. Synthesis of anti-angina drug ranolazine. 广西大学学报，自然科学版，28: 301～303

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)	13182	Guaiacol; 2-Methoxyphenol	90-05-1	C₇H₈O₂	详情	详情
(II)	10146	Epichlorohydrin; 2-(Chloromethyl)oxirane	106-89-8	C₃H₅ClO	详情	详情
(III)	24103	2-[(2-methoxyphenoxy)methyl]oxirane		C₁₀H₁₂O₃	详情	详情
(IV)	17527	2,6-Xylidine; 2,6-Dimethylaniline; 2,6-Dimethylphenylamine	87-62-7	C₈H₁₁N	详情	详情
(V)	24100	2-chloro-N-(2,6-dimethylphenyl)acetamide	2198-53-0	C₁₀H₁₂ClNO	详情	详情
(VI)	24102	N-(2,6-dimethylphenyl)-2-(1-piperazinyl)acetamide		C₁₄H₂₁N₃O	详情	详情

合成路线6

该中间体在本合成路线中的序号：(II)

参考文献中间体

合成目标

【1】 Yan J．2007. Synthesis of ranolazine.中国专利申请公开说明书．CN 1915982

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)	17527	2,6-Xylidine; 2,6-Dimethylaniline; 2,6-Dimethylphenylamine	87-62-7	C₈H₁₁N	详情	详情
(II)	24100	2-chloro-N-(2,6-dimethylphenyl)acetamide	2198-53-0	C₁₀H₁₂ClNO	详情	详情
(III)	24102	N-(2,6-dimethylphenyl)-2-(1-piperazinyl)acetamide		C₁₄H₂₁N₃O	详情	详情
(IV)	10146	Epichlorohydrin; 2-(Chloromethyl)oxirane	106-89-8	C₃H₅ClO	详情	详情
(V)	13182	Guaiacol; 2-Methoxyphenol	90-05-1	C₇H₈O₂	详情	详情
(VI)	24103	2-[(2-methoxyphenoxy)methyl]oxirane		C₁₀H₁₂O₃	详情	详情

Extended Information