二乙胺 → 7-Chloro-2-[2-(diethylamino)ethyl]-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepin-5(4H)-one oxalate

HRID 4862

反应方程式

HRID 4862 反应方程式
[Cl:1][C:2]1[CH:12]=[N:11][C:10]2[O:9][CH:8]([CH2:13][CH2:14]Cl)[CH2:7][N:6]([CH3:16])[C:5](=[O:17])[C:4]=2[CH:3]=1.[CH2:18]([NH:20][CH2:21][CH3:22])[CH3:19].C([O:25][C:26](=[O:28])C)C.[CH3:29][OH:30].[OH-:31].[NH4+]>C(O)C>[C:26]([OH:28])(=[O:25])[C:29]([OH:31])=[O:30].[Cl:1][C:2]1[CH:12]=[N:11][C:10]2[O:9][CH:8]([CH2:13][CH2:14][N:20]([CH2:21][CH3:22])[CH2:18][CH3:19])[CH2:7][N:6]([CH3:16])[C:5](=[O:17])[C:4]=2[CH:3]=1

参与物

6

反应物 4

HCID 8021二乙胺3 次HCID 14923氨水HCID 137264457-Chloro-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepin-5(4H)-oneHCID 21584119Ethylacetate methanol

产物 1

HCID 137265987-Chloro-2-[2-(diethylamino)ethyl]-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepin-5(4H)-one oxalate收率 76%

试剂、催化剂与溶剂 1

HCID 702乙醇溶剂

实验过程

To a suspension of 7-chloro-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepine-5(4H)-one in 50 ml of absolute ethanol was added 2.26 ml (0.022 mole) of diethylamine and the mixture heated to reflux. (Complete dissolution occurred). After 1 hr, another 2.26 ml (0.022 mole) of diethylamine was added followed by 5.0 ml (0.049 mole) and heating continued for 2 more hours. TLC (ethylacetate/methanol/conc. ammonium hydroxide, 7:2:1, v/v/v) still showed presence of starting material; another 2.26 ml (0.022 mole) of diethylamine was added and heating continued for 15 hr at reflux. Solvent was removed by rotary evaporation (60° C., 30 mm Hg) and the residue taken up in methylene chloride, washed twice with dilute aqueous sodium hydroxide and once with water. The organic layer was dried over sodium sulfate, filtered and concentrated by rotary evaporation, and azeotroped once with toluene. The oil was treated with oxalic acid in isopropyl alcohol which yielded 6.7 g (76%) of white crystals, m.p. 163°-164° C.

后处理

  1. temperaturethe mixture heated to reflux
  2. dissolution(Complete dissolution occurred)
  3. temperatureheating
  4. temperatureheating
  5. waitcontinued for 15 hr
  6. temperatureat reflux
  7. customSolvent was removed by rotary evaporation (60° C., 30 mm Hg)
  8. washwashed twice with dilute aqueous sodium hydroxide and once with water
  9. dry with materialThe organic layer was dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated by rotary evaporation
  12. customazeotroped once with toluene
  13. additionThe oil was treated with oxalic acid in isopropyl alcohol which

来源与证据

ORD记录
ord-f16fdd29c044474da886cbfb04a2815b
来源数据集
uspto-grants-1988_02
专利号
US04727152

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