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

HRID 356195

Reaction equation

HRID 356195 reaction equation
[C:1]1(=[O:8])[NH:6][C:5](=[O:7])[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:11]([N:18]1[C:24](=[O:25])[C@H:23]2CCC[C@H]2[N:21]([C:29](=[O:32])[CH2:30]Br)[C:20]2[CH:33]=[CH:34][CH:35]=[CH:36][C:19]1=2)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[NH4+]>CN(C)C=O>[CH2:15]([CH:16]1[CH:30]2[CH:11]([N:18]([C:24](=[O:25])[CH2:23][N:6]3[C:5](=[O:7])[CH2:4][CH2:3][CH2:2][C:1]3=[O:8])[C:19]3[CH:36]=[CH:35][CH:34]=[CH:33][C:20]=3[NH:21][C:29]2=[O:32])[CH2:12][CH2:17]1)[C:14]1[CH:13]=[CH:4][CH:3]=[CH:2][CH:1]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 70726GlutarimideHCID 70109710(3aR*,10aS*)-9-benzyl-4-(bromoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]-cyclopenta[e][1,4]diazepin-10(1H)-one

Product 1

HCID 86753323Benzyl-4-(glutarimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]-diazepin-10(1H)-oneYield 114.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of glutarimide (136 mg, 1.2 mmol) in N,N-dimethylformamide (2 mL) was added, at 0° C., sodium hydride (60% liquid paraffin dispersion, 44 mg, 1.1 mmol), and the mixture was stirred for 5 minutes. To this mixture was added (3aR*,10aS*)-9-benzyl-4-(bromoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]-cyclopenta[e][1,4]diazepin-10(1H)-one (413 mg, 1 mmol), and the mixture was stirred for 30 minutes at room temperature. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride (4 mL), which was subjected to extraction twice with chloroform. Organic layers were combined, washed with water and dried over magnesium sulfate, which was subjected to filtration, and the filtrate was concentrated under reduced pressure. The concentrate was crystallized from ethyl acetate-diethyl ether to give 305 mg (yield 68%) of the titled compound, m.p. 220°-221° C.

Workup

  1. extractionwas subjected to extraction twice with chloroform
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate, which
  4. filtrationwas subjected to filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe concentrate was crystallized from ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-bfa728810a9f4ffea5191033a67ef55a
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Linked notes

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