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【结 构 式】

【分子编号】64194

【品名】3-chloropropyl methanesulfonate

【CA登记号】

【 分 子 式 】C4H9ClO3S

【 分 子 量 】172.63236

【元素组成】C 27.83% H 5.25% Cl 20.54% O 27.8% S 18.57%

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:(IV)

This compound has been obtained by several related ways. 1.- The condensation of 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5- carbonitrile (I) with 3-chloropropyl tosylate (II) by means of LDA in THF gives 1-(4-fluorophenyl)-1-(3-tosyloxypropyl)-1,3-dihydroisobenzofuran-5-carbonitrile (III), which is then condensed with dimethylamine in hot DMF to yield the target citalopram. 2.- The condensation of 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5- carbonitrile (I) with 3-chloropropyl mesylate (IV) by means of LDA in THF gives 1-(4-fluorophenyl)-1-(3-mesyloxypropyl)-1,3-dihydroisobenzofuran-5- carbonitrile (V), which is then condensed with sodium azide in hot DMF to yield the corresponding azido derivative (VI). The reduction of (VI) with H2 over Pd/C in ethanol affords the 3-aminopropyl derivative (VII), which is finally reductively methylated with formaldehyde and NaBH3CN in methanol to provide the target citalopram. 3.- The reaction of mesylate (V) with methylamine in THF gives the corresponding methylaminopropyl derivative (VIII), which is finally methylated by means of HCHO in refluxing HCOOH to yield the target citalopram. 4.- The direct condensation of mesylate (V) with dimethylamine in hot ethanol/THF also gives the target citalopram.

1 Rock, M.H.; Ahmadian, H. (H. Lundbeck A/S); Method for the preparation of citalopram. CA 2401374; EP 1263750; FR 2805814; JP 2003519692; US 2003092761; WO 0151478 .
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) 33233 1-(4-fluorophenyl)-5-phtalancarbonitrile; 1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile C15H10FNO 详情 详情
(II) 55581 3-Chloropropyl-p-toluenesulfonate C10H13ClO3S 详情 详情
(III) 55301 3-[5-cyano-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-1-yl]propyl 4-methylbenzenesulfonate C25H22FNO4S 详情 详情
(IV) 64194 3-chloropropyl methanesulfonate C4H9ClO3S 详情 详情
(V) 55302 3-[5-cyano-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-1-yl]propyl methanesulfonate C19H18FNO4S 详情 详情
(VI) 55303 1-(3-azidopropyl)-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile C18H15FN4O 详情 详情
(VII) 55304 1-(3-aminopropyl)-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile C18H17FN2O 详情 详情
(VIII) 64195 1-(4-fluorophenyl)-1-[3-(methylamino)propyl]-1,3-dihydro-2-benzofuran-5-carbonitrile C19H19FN2O 详情 详情
Extended Information