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【结 构 式】

【分子编号】10992

【品名】[4-(4-fluorophenyl)-1-methyl-3-piperidinyl]methyl benzenesulfonate

【CA登记号】

【 分 子 式 】C19H22FNO3S

【 分 子 量 】363.4530232

【元素组成】C 62.79% H 6.1% F 5.23% N 3.85% O 13.21% S 8.82%

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:(V cis+trans)

A synthesis of [14C]-paroxetine labeled at the -CH2O- group has been described: 4-(4-Fluorophenyl)-1-methyl-1,2,5,6-tetrahydropyridine (I) is hydroxymethylated with [14C]-formaldehyde (II), yielding 4-(4-fluorophenyl)-1-methyl-1,2,5,6-tetrahydropyridine-3-methanol (III), which is hydrogenated with H2 over Pd/C in ethanol to give 4-(4-fluorophenyl)-1-methylpiperidine-3-methanol (IV) as a mixture of cis- and trans-isomers. The reaction of (IV) with phenylsulfonyl chloride and NaOH in water affords the corresponding sulfonate (V), which is then condensed with 3,4-(methylenedioxy)phenol (VI) by means of NaOH in toluene-4-methyl-2-pentanol, giving 4-(4-fluorophenyl)-1-methyl-3-[3,4-(methylenedioxy)phenoxymethyl]piperi dine (VII). The chromatographic separation of the trans-isomer of (VII), followed by its optical resolution with L-(+)-tartaric acid, affords optically pure (-)-(3S,4R)-N-methylparoxetine (VIII), which is finally demethylated with vinyl chloroformate and dry HCl.

1 Willcocks, K.; Rustidge, D.C.; Barnes, R.D.; Tidy, D.J.D.; The synthesis of [14C]-3S,4R-4-(4-fluorophenyl)-3-(3,4-methylenedioxyp henoxymethyl)piperidine hydrochloride (BRL 29060A), and mechanistic studies using carbon-13 labelling. J Label Compd Radiopharm 1993, 33, 8, 783.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV cis+trans) 10991 [4-(4-Fluorophenyl)-1-methyl-3-piperidinyl]methanol C13H18FNO 详情 详情
(V cis+trans) 10992 [4-(4-fluorophenyl)-1-methyl-3-piperidinyl]methyl benzenesulfonate C19H22FNO3S 详情 详情
(IV cis+trans) 45035 [4-(4-fluorophenyl)-1-methyl-3-piperidinyl]methanol C13H18FNO 详情 详情
(V cis+trans) 45036 [4-(4-fluorophenyl)-1-methyl-3-piperidinyl]methyl benzenesulfonate C19H22FNO3S 详情 详情
(I) 10989 4-(4-Fluorophenyl)-1-methyl-1,2,3,6-tetrahydropyridine C12H14FN 详情 详情
(III) 10990 [4-(4-Fluorophenyl)-1-methyl-1,2,3,6-tetrahydro-3-pyridinyl]methanol C13H16FNO 详情 详情
(III) 45034 [4-(4-fluorophenyl)-1-methyl-1,2,3,6-tetrahydro-3-pyridinyl]methanol C13H16FNO 详情 详情
(VI) 10985 1,3-Benzodioxol-5-ol; Sesamol 533-31-3 C7H6O3 详情 详情
(VII) 10994 1,3-Benzodioxol-5-yl [4-(4-fluorophenyl)-1-methyl-3-piperidinyl]methyl ether; 3-[(1,3-Benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-1-methylpiperidine C20H22FNO3 详情 详情
(VII) 45037 1,3-benzodioxol-5-yl [4-(4-fluorophenyl)-1-methyl-3-piperidinyl]methyl ether; 3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-1-methylpiperidine C20H22FNO3 详情 详情
(VIII) 10987 (3S,4R)-3-[(1,3-Benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-1-methylhexahydropyridine; 1,3-Benzodioxol-5-yl [(3S,4R)-4-(4-fluorophenyl)-1-methylhexahydro-3-pyridinyl]methyl ether C20H22FNO3 详情 详情
(VIII) 45038 (3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-1-methylpiperidine; 1,3-benzodioxol-5-yl [(3S,4R)-4-(4-fluorophenyl)-1-methylpiperidinyl]methyl ether C20H22FNO3 详情 详情
Extended Information