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

Reaction equation

HRID 356169 reaction equation
[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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1d7f9929ab594b6bbdc20b20d4bea05d
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Linked notes

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