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【结 构 式】

【分子编号】14852

【品名】2-chloro-N-(7-hydroxy-2,2,4,6-tetramethyl-2,3-dihydro-1H-inden-1-yl)acetamide

【CA登记号】

【 分 子 式 】C15H20ClNO2

【 分 子 量 】281.78204

【元素组成】C 63.94% H 7.15% Cl 12.58% N 4.97% O 11.36%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VI)

Alkylation of 4,6-dimethyl-7-hydroxy-1-indanone (I) with methyliodide and sodium hydride in DMF affords 7-methoxy-2,2,4,6-tetramethyl-1-indanone (II), which is demethylated with aluminum chloride in CH3CN to give 7-hydroxy-2,2,4,6-tetramethyl-1-indanone (III). Oxime formation with hydroxylamine hydrochloride in pyridine yields 7-hydroxy-2,2,4,6-tetramethyl-1-indanone oxime (IV), which on treatment with hydrogen in the presence of platinum oxide in acetic acid gives 1-amino-7-hydroxy-2,2,4,6-tetramethylindan (V) (1, 3). Acetylation of (V) with chloroacetyl chloride and triethylamine gives 2-chloro-N-(7-hydroxy-2,2,4,6-tetramethylindan-1-yl)acetamide (VI), which is finally condensed with 1-(3-methoxyphenyl)piperazine (VII) in acetonitrile.

1 Oshiro, Y.; Ueda, H.; Nakagawa, K. (Otsuka Pharmaceutical Co., Ltd.); 2,3-Dihydro-1H-indene derivs., a process for preparing them and pharmaceutical compsns. containing same. EP 0173331; ES 8800121; ES 8800884; ES 8801180; JP 1986069747; JP 1987129258; JP 1993004950; US 4788130; US 4895847; US 5242919 .
2 Oshiro, Y.; Tottori, K.; Tanaka, T.; Kikuchi, T.; Sakurai, Y.; Ueda, H.; Novel cerebroprotective agents with central nervous system stimulating activity. 1. Synthesis and pharmacology of 1-amino-7-hydroxyindan derivatives. J Med Chem 1991, 34, 7, 2004-13.
3 Mealy, N.; Prous, J.; Castaner, J.; OPC-14117. Drugs Fut 1993, 18, 8, 707.
4 Tottori, K.; Tanaka, T.; Hirose, T.; Sakurai, Y.; Kikuchi, T.; Oshiro, Y.; Novel cerebroprotective agents with central nervous system stimulating activity. 2. Synthesis and pharmacology of the 1-(acylamino)-7-hydroxyindan derivatives. J Med Chem 1991, 34, 7, 2014-23.
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) 14847 7-hydroxy-4,6-dimethyl-1-indanone C11H12O2 详情 详情
(II) 14848 7-methoxy-2,2,4,6-tetramethyl-1-indanone C14H18O2 详情 详情
(III) 14849 7-hydroxy-2,2,4,6-tetramethyl-1-indanone C13H16O2 详情 详情
(IV) 14850 7-hydroxy-2,2,4,6-tetramethyl-1-indanone oxime C13H17NO2 详情 详情
(V) 14851 3-amino-2,2,5,7-tetramethyl-4-indanol C13H19NO 详情 详情
(VI) 14852 2-chloro-N-(7-hydroxy-2,2,4,6-tetramethyl-2,3-dihydro-1H-inden-1-yl)acetamide C15H20ClNO2 详情 详情
(VII) 14853 methyl 3-piperazinophenyl ether; 1-(3-methoxyphenyl)piperazine 16015-71-7 C11H16N2O 详情 详情
Extended Information