4-benzyl-2-[[(4-ethoxy-3-thienyl)oxy]methyl]morpholine; 4-[(4-benzyl-2-morpholinyl)methoxy]-3-thienyl ethyl ether -Drug Synthesis Database

【结构式】

【分子编号】34732

【品名】4-benzyl-2-[[(4-ethoxy-3-thienyl)oxy]methyl]morpholine; 4-[(4-benzyl-2-morpholinyl)methoxy]-3-thienyl ethyl ether

【CA登记号】

【分子式】C₁₈H₂₃NO₃S

【分子量】333.45156

【元素组成】C 64.84% H 6.95% N 4.2% O 14.39% S 9.62%

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：(VII)

In an alternative method, ring opening of epoxide (I) with benzylamine produced aminoalcohol (III). Subsequent coupling of (III) with chloroacetyl chloride (IV) yielded chloroacetamide (V), which was cyclized to the morpholinone (VI) upon treatment with NaOMe in MeOH. Reduction of the lactam function of (VI) with LiAlH4 gave the N-benzyl morpholine (VII). Finally, the N-benzyl group of (VII) was cleaved by hydrogenolysis using Pearlman's catalyst.

参考文献中间体

合成目标

【1】 Corral, C.; Lissavetzky, J.; Sánchez-Mateo, C.C.; Darias, V.; Expósito-Orta, M.A.; Martín-Conde, J.A.; Manzanares, I.; Synthesis and preliminary pharmacological evaluation of thiophene analogues of viloxazine as potential antidepressant drugs. Bioorg Med Chem 1999, 7, 7, 1349.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	15147	Benzylamine; Phenylmethanamine	100-46-9	C₇H₉N	详情	详情
(I)	34727	4-ethoxy-3-thienyl 2-oxiranylmethyl ether; 2-[[(4-ethoxy-3-thienyl)oxy]methyl]oxirane		C₉H₁₂O₃S	详情	详情
(III)	34729	1-(benzylamino)-3-[(4-ethoxy-3-thienyl)oxy]-2-propanol		C₁₆H₂₁NO₃S	详情	详情
(IV)	11296	2-Chloroacetyl chloride; Chloroacetic chloride	79-04-9	C₂H₂Cl₂O	详情	详情
(V)	34730	N-benzyl-2-chloro-N-[3-[(4-ethoxy-3-thienyl)oxy]-2-hydroxypropyl]acetamide		C₁₈H₂₂ClNO₄S	详情	详情
(VI)	34731	4-benzyl-6-[[(4-ethoxy-3-thienyl)oxy]methyl]-3-morpholinone		C₁₈H₂₁NO₄S	详情	详情
(VII)	34732	4-benzyl-2-[[(4-ethoxy-3-thienyl)oxy]methyl]morpholine; 4-[(4-benzyl-2-morpholinyl)methoxy]-3-thienyl ethyl ether		C₁₈H₂₃NO₃S	详情	详情

Extended Information