4-(N-Methyl-benzylamino)-1,1-diethoxy-butan | 94329-43-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(N-Methyl-benzylamino)-1,1-diethoxy-butan
• 英文别名: 4-(N-benzyl-N-methylamino)butyraldehyde diethyl acetal；N-benzyl-4,4-diethoxy-N-methylbutan-1-amine
• CAS: 94329-43-8
• 化学式: C₁₆H₂₇NO₂
• 分子量: 265.396
• InChiKey: QQMFOPFJADTZEW-UHFFFAOYSA-N

物化性质

• 沸点：
  140-150 °C(Press: 0.5 Torr)
• 密度：
  0.966±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-苄基-3-氯-N-甲基正丙胺 、 原甲酸三乙酯 在 碘 、 magnesium 作用下， 以 环己烷 为溶剂， 反应 5.33h， 以67.5%的产率得到4-(N-Methyl-benzylamino)-1,1-diethoxy-butan
  参考文献：
  名称：

  [EN] PREPARATION OF 4-(N, N-DISUBSTITUTEDAMINO) BUTYRALDEHYDE ACETALS
  [FR] PROCEDE AMELIORE POUR L'ELABORATION D'ACETALS DE 4-(N, N-AMINODISUBSTITUE) BUTYRALDEHYDE

  摘要：

  公开号：

  WO2003101931A3

文献信息

• [EN] AN IMPROVED PROCESS FOR THE PREPARATION OF 4-(N, N-DISUBSTITUTEDAMINO) BUTYRALDEHYDE ACETALS<br/>[FR] PROCEDE AMELIORE POUR L'ELABORATION D'ACETALS DE 4-(N, N-AMINODISUBSTITUE) BUTYRALDEHYDE
  申请人：NATCO PHARMA LTD

  公开号：WO2003101931A2

  公开（公告）日：2003-12-11

  The invention disclosed in this application relates to an improved process for the preparation of compounds of formula (I): R1R2NCH2CH2CH2CH(OR3)2; wherein, R1 = R2 = C1-C16 alkyl; C3-C7 cycloalkyl; R1 = C1-C16 alkyl; R2 = C3-C7 cycloalkyl; NR1R2 = pyrrolidino, piperidino, morpholino, thiomorpholino, R1 = C1-C6 alkyl; R2 = ArCH2; Ar =4-R4-C6H4-, R4 = MeO, EtO, Me, Et, NMe2, NEt2, SMe, SEt, etc; R3=C1-C6 alkyl; C3-C7 cycloalkyl which comprises: (i) Reacting 3-(N, N-disubstitutedamino)propyl halide of formula (XXI): R1R2NCH2CH2CH2X; wherein, R1, R2 = as defined above, X = C1 or Br, with magnesium in the presence of a solvent to get the Grrgnard reagent 3-(N, N-disubstitutedamino)-propylmagnesium halide; (ii) Reacting the resulting 3-(N, N-disubstitutedamino) propylmagnesium halide (Grignard reagent) with the trisubstituted orthoformate of formula (XVII): HC(OR5)(OR3)2; wherein, R3 and R5 is same or different and represent C1 to C6 alkyl, C3 to C7 cycloalkyl OR R3 is as defined above and R5 represents phenyl radical; (iii) Filtering off the resultant reaction mixture and distilling the filtrate to isolate the compound of the formula (I). These substituted butyraldehyde derivatives of the formula (I) are very important building blocks for the synthesis of various tryptamine derivatives. In particular 4-(N, N-dimethylamino)butyraldehyde dimethyl or diethyl acetals are crucial intermediates for the synthesis of commercially available anti-migraine drugs, like sumatriptan, zolmitriptan, and rizatriptan.
• [EN] PREPARATION OF 4-(N, N-DISUBSTITUTEDAMINO) BUTYRALDEHYDE ACETALS<br/>[FR] PROCEDE AMELIORE POUR L'ELABORATION D'ACETALS DE 4-(N, N-AMINODISUBSTITUE) BUTYRALDEHYDE
  申请人：——

  公开号：WO2003101931A3

  公开（公告）日：2005-08-18