(2S)-2-piperidinecarbonyl chloride -Drug Synthesis Database

【结构式】

【分子编号】19499

【品名】(2S)-2-piperidinecarbonyl chloride

【CA登记号】

【分子式】C₆H₁₀ClNO

【分子量】147.60424

【元素组成】C 48.82% H 6.83% Cl 24.02% N 9.49% O 10.84%

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)

Optical resolution of DL-pipecolinic acid (I) with (+)-tartaric acid gives L-pipecolinic acid (II), which is treated with PCl5 to obtain acil chloride (III). This compound is condensed with 2,5-dimethylaniline (IV) by means N-methylpirrolidine (NMP) to afford amide (V). Finally, amide (V) is alkylated with 1-bromopropane by means potassium carbonate (K2CO3) to yield Ropivacaine.

参考文献中间体

合成目标

【1】 Sandeberg, R.V. (AstraZeneca plc); S-(-)-1-propyl-2',6'-pipecoloxylidide hydrochloride monohydrate, process for its preparation and pharmaceutical preparation containing it. EP 0239710; US 4870086 .
【2】 T. af Ekenstam, B.; Bovin, C. (Alpharma Inc.); L-N-n-Propylpipecolic acid-2,6-xylidide and method for preparing the same. JP 1985502054; WO 8500599 .

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)	17532	2-piperidinecarboxylic acid; pipecolic acid	535-75-1	C₆H₁₁NO₂	详情	详情
(II)	17380	(2S)hexahydro-2-pyridinecarboxylic acid; (S)-pipecolic acid	3105-95-1	C₆H₁₁NO₂	详情	详情
(III)	19499	(2S)-2-piperidinecarbonyl chloride		C₆H₁₀ClNO	详情	详情
(IV)	17527	2,6-Xylidine; 2,6-Dimethylaniline; 2,6-Dimethylphenylamine	87-62-7	C₈H₁₁N	详情	详情
(V)	17531	(2S)-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide		C₁₄H₂₀N₂O	详情	详情
(VI)	19502	Propyl bromide; 1-Bromopropane	106-94-5	C₃H₇Br	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

1) The optical resolution of pipecolic acid (I) with (+)-tartaric acid in water-ethanol gives L-pipecolic acid (II), which by reaction with Cl5P in acetyl chloride is converted to the acyl chloride (III). The condensation of (III) with 2,6-xylidine (IV) by means of N-methylpyrrolidone (NMP) in acetone affords L-pipecolic acid 2,6-xylidide (V), which is finally alkylated with propyl bromide (VI) and K2CO3 in hot isopropanol.

参考文献中间体

合成目标

【1】 T. af Ekenstam, B.; Bovin, C. (Astra Lakemedel AB); L-N-n-Propylpipecolic acid 2,6-xylidide. US 4695576 .
【2】 Prous, J.; Castaner, J.; ROPIVACAINE HYDROCHLORIDE < Rec INNM >. Drugs Fut 1989, 14, 8, 767.

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)	17532	2-piperidinecarboxylic acid; pipecolic acid	535-75-1	C₆H₁₁NO₂	详情	详情
(II)	17380	(2S)hexahydro-2-pyridinecarboxylic acid; (S)-pipecolic acid	3105-95-1	C₆H₁₁NO₂	详情	详情
(III)	19499	(2S)-2-piperidinecarbonyl chloride		C₆H₁₀ClNO	详情	详情
(IV)	17527	2,6-Xylidine; 2,6-Dimethylaniline; 2,6-Dimethylphenylamine	87-62-7	C₈H₁₁N	详情	详情
(V)	17531	(2S)-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide		C₁₄H₂₀N₂O	详情	详情
(VI)	19502	Propyl bromide; 1-Bromopropane	106-94-5	C₃H₇Br	详情	详情

Extended Information