Hydrochloric Acid → 1-(6-ethoxycarbonylhexyl)-3-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-2,4-(1H,3H)quinazolinedione dihydrochloride

HRID 483235

반응식

HRID 483235 반응식
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][N:19]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][C:20]2=[O:30])[CH2:13][CH2:12]1.Br[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39].[ClH:43]>CN(C)C=O.C(O)C>[ClH:43].[ClH:43].[CH2:41]([O:40][C:38]([CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:28](=[O:29])[N:19]([CH2:18][CH2:17][N:14]2[CH2:13][CH2:12][N:11]([C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[O:4][CH3:3])[CH2:16][CH2:15]2)[C:20]1=[O:30])=[O:39])[CH3:42]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 1220653-[2-[4-(2-Methoxyphenyl)-1-piperazinyl]ethyl]-2,4(1H,3H)-quinazolinedioneHCID 122490Ethyl 7-bromoheptanoate

생성물 1

HCID 202428551-(6-ethoxycarbonylhexyl)-3-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-2,4-(1H,3H)quinazolinedione dihydrochloride

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6228Dimethylformamide용매2회

반응 조건

온도
50 °C

실험 절차

To a suspension of 60% sodium hydride (0.44 g) in dimethylformamide (50 ml), was added 3-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-2,4-(1H,3H)quinazolinedione (3.80 g) in a small portion under a nitrogen stream, and the mixture was stirred at room temperature for 30 minutes and at 50° C. for 10 minutes. After cooling to room temperature, a solution of ethyl 7-bromoheptanoate (2.37 g) in dimethylformamide (20 ml) was added to the mixture and the resulting mixture was stirred at room temperature overnight. The solvent was distilled off under vacuum and the resulting residue was extracted with chloroform. The chloroform layer was washed with water and dried with sodium sulfate. When the solvent was distilled off under vacuum, an oily substance was obtained and upon column chromatography on silica gel (eluted with a chloroformethanol 25:1 mixture), a pale yellow oil of 1-(6-ethoxycarbonylhexyl)-3-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-2,4-(1H, 3H)quinazolinedione (3.62 g) was obtained. The oil was dissolved in ethanol (50 ml) and hydrogen chloride gas was introduced into the solution for about 5 minutes. After distilling off the solvent, the crystalline residue was recrystallized from a mixture of ethanol and n-hexane to give colorless needles of 1-(6-ethoxycarbonylhexyl)-3-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-2,4-(1H,3H)quinazolinedione dihydrochloride (3.45 g) having a m.p. of 109°-111° C.

후처리

  1. temperatureAfter cooling to room temperature
  2. stirringthe resulting mixture was stirred at room temperature overnight
  3. distillationThe solvent was distilled off under vacuum
  4. extractionthe resulting residue was extracted with chloroform
  5. washThe chloroform layer was washed with water
  6. dry with materialdried with sodium sulfate
  7. distillationWhen the solvent was distilled off under vacuum
  8. customan oily substance was obtained and upon column chromatography on silica gel (
  9. washeluted with a chloroformethanol 25:1 mixture), a pale yellow oil of 1-(6-ethoxycarbonylhexyl)-3-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-2,4-(1H, 3H)quinazolinedione (3.62 g)
  10. customwas obtained
  11. distillationAfter distilling off the solvent
  12. customthe crystalline residue was recrystallized from a mixture of ethanol and n-hexane

출처 및 근거

ORD 기록
ord-caaddd4d34324e56bb2b285c72e9785e
출처 데이터셋
uspto-grants-1986_03
특허 번호
US04578465

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