二甲胺 → 1-(7-Fluoro-1H-indol-3-yl)-N,N-dimethylmethanamine

HRID 401601

反应方程式

HRID 401601 反应方程式
C=O.[CH3:3][NH:4][CH3:5].[F:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:15]=1[NH:14][CH:13]=[CH:12]2.[C:16]([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>C(O)(=O)C>[F:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:5]=1[NH:4][CH:3]=[C:12]2[CH2:13][N:14]([CH3:15])[CH3:16]

参与物

7

反应物 5

HCID 674二甲胺HCID 712多聚甲醛HCID 11430碳酸钾HCID 14798二甲基对苯二胺二盐酸HCID 27745047-氟吲哚

产物 1

HCID 249051291-(7-Fluoro-1H-indol-3-yl)-N,N-dimethylmethanamine收率 74%

试剂、催化剂与溶剂 1

HCID 176醋酸溶剂

实验过程

To a mixture of acetic acid (13.6 mL) and formaldehyde (0.340 mL, 4.5 mmol, 37% solution) under argon was added dimethyl amine (2.05 mL, 16.3 mmol., 40% solution). The reaction mixture was stirred for 10 min and then treated with 7-fluoroindole (540 mg, 4.0 mmol.). The resulting mixture was stirred at room temperature for ˜16 h. The reaction mixture was first neutralized with K2CO3 and then basified with NaOH (2N), and then extracted in ethyl acetate, washed with water, dried, and concentrated. Solid obtained was recrystallized from ethyl acetate and hexane to give (7-Fluoro-1H-indol-3-ylmethyl)dimethylamine (570 mg, 74%): mp 133-137° C., 1H NMR (500 MHz, CDCl3): 2.31 (s, 6H), 3.62 (s, 2H), 6.88-6.92 (dd, J=8.0 and 8.0 Hz, 1H), 7.00-7.04 (m, 1H), 7.16 (d, J=2.5 Hz, 1H), 7.46 (d, J=8.0 Hz, 1H), 8.34 (s, 1H).

后处理

  1. stirringThe resulting mixture was stirred at room temperature for ˜16 h
  2. extractionextracted in ethyl acetate
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customSolid obtained
  7. customwas recrystallized from ethyl acetate and hexane

来源与证据

ORD记录
ord-6711a7e76634456d918f9239b1ac69bc
来源数据集
uspto-grants-2014_06
专利号
US08741942B2

关联笔记

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