Sodium hydride → 9-(2-Methoxybenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

HRID 356169

반응식

HRID 356169 반응식
[C:1]1(=[O:29])[N:5]([CH2:6][C:7]([N:9]2[CH:15]3[CH2:16][CH2:17][CH2:18][CH:14]3[C:13](=[O:19])[NH:12][C:11]3[CH:20]=[CH:21][CH:22]=[CH:23][C:10]2=3)=[O:8])[C:4](=[O:24])[C:3]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:2]12.[H-].[Na+].[CH3:32][O:33][C:34]1[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=1[CH2:36]Br.[Cl-].[NH4+]>CN(C)C=O.O>[CH3:32][O:33][C:34]1[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=1[CH2:36][N:12]1[C:13](=[O:19])[CH:14]2[CH2:18][CH2:17][CH2:16][CH:15]2[N:9]([C:7](=[O:8])[CH2:6][N:5]2[C:4](=[O:24])[C:3]3=[CH:25][CH:26]=[CH:27][CH:28]=[C:2]3[C:1]2=[O:29])[C:10]2[CH:23]=[CH:22][CH:21]=[CH:20][C:11]1=2

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 403081-(Bromomethyl)-2-methoxybenzeneHCID 189405414-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

생성물 1

HCID 189406279-(2-Methoxybenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one수율 46%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a suspension of 4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (389 mg, 1.0 mmol) in N,N-dimethylformamide (3 mL) was added sodium hydride (60% liquid paraffin dispersion, 44 mg, 1.1 mmol). The mixture was stirred for 10 minutes at room temperature. To this mixture was added 2-methoxybenzyl bromide (241 mg, 1.2 mmol), which was stirred for 90 minutes at room temperature. To the reaction mixture was added a saturated aqueous solution of ammonium chloride (3 mL), which was diluted with water. The resulting solid was collected by filtration, which dissolved in chloroform. The solution was dried over magnesium sulfate, which was subjected to filtration, and the filtrate was concentrated under reduced pressure. The concentrate was recrystallized from chloroform-ethanol to give 234 mg (yield 46%) of a mixture of cis-compound and trans-compound. m.p. 261°-272° C.

후처리

  1. stirringwas stirred for 90 minutes at room temperature
  2. filtrationThe resulting solid was collected by filtration, which
  3. dissolutiondissolved in chloroform
  4. dry with materialThe solution was dried over magnesium sulfate, which
  5. filtrationwas subjected to filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe concentrate was recrystallized from chloroform-ethanol

출처 및 근거

ORD 기록
ord-1d7f9929ab594b6bbdc20b20d4bea05d
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834463

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