4-chloro-1-(1-pyrrolidinyl)-1-butanone -Drug Synthesis Database

【结构式】

【分子编号】33782

【品名】4-chloro-1-(1-pyrrolidinyl)-1-butanone

【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 1 条

合成路线1

该中间体在本合成路线中的序号：(IX)

Ethyl isonipecotate (I) was protected as the N-trityl derivative (II) using triphenylmethyl chloride and triethylamine. Addition of Grignard reagent (IV) (prepared from 1-bromo-4-fluorobenzene (III) and magnesium in Et2O) to (II) produced the diaryl carbinol (V). Alcohol dehydration with simultaneous trityl group cleavage under acidic conditions yielded 4-[bis(4-fluorophenyl)methylene]piperidine (VI). 4-Chlorobutyrylpyrrolidine (IX), prepared by coupling of 4-chlorobutyryl chloride (VII) and pyrrolidine (VIII), was then condensed with piperidine (VI) to yield the target compound.

参考文献中间体

合成目标

【1】 Rae, D.R.; Jaap, D.R. (Akzo Nobel N.V.); Diphenylmethylene piperidine derivs.. EP 0842170; JP 1999508907; US 5935974; WO 9703065 .

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)	17410	Ethyl isonipecotate; ethyl 4-piperidinecarboxylate	1126-09-6	C₈H₁₅NO₂	详情	详情
(II)	33780	ethyl 1-trityl-4-piperidinecarboxylate		C₂₇H₂₉NO₂	详情	详情
(III)	29012	1-bromo-4-fluorobenzene	460-00-4	C₆H₄BrF	详情	详情
(IV)	13643	4-fluorophenyl magnesium bromide;Bromo(4-fluorophenyl)magnesium;bromo(p-fluorophenyl)Magnesium;p-Fluorophenylmagnesium bromide	352-13-6	C₆H₄BrFMg	详情	详情
(V)	33781	bis(4-fluorophenyl)(1-trityl-4-piperidinyl)methanol		C₃₇H₃₃F₂NO	详情	详情
(VI)	24706	4-[bis(4-fluorophenyl)methylene]piperidine		C₁₈H₁₇F₂N	详情	详情
(VII)	11265	4-Chlorobutanoyl chloride; 4-Chlorobutyric acid chloride	4635-59-0	C₄H₆Cl₂O	详情	详情
(VIII)	11376	Pyrrolidine	123-75-1	C₄H₉N	详情	详情
(IX)	33782	4-chloro-1-(1-pyrrolidinyl)-1-butanone		C₈H₁₄ClNO	详情	详情

Extended Information