2H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo- → (3aR*,10aS*)-9-(4-Chlorobenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]-diazepine-10(1H)-one

HRID 356188Notes

Reaction equation

HRID 356188 reaction equation
Cl.[Cl:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][N:8]2[C:14](=[O:15])[C@H:13]3[CH2:16][CH2:17][CH2:18][C@H:12]3[NH:11][C:10]3[CH:19]=[CH:20][CH:21]=[CH:22][C:9]2=3)=[CH:5][CH:4]=1.[C:25]1(=[O:39])[N:29]([CH2:30][C:31](Cl)=[O:32])[C:28](=[O:34])[C:27]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:26]12.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Cl:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][N:8]2[C:14](=[O:15])[C@H:13]3[CH2:16][CH2:17][CH2:18][C@H:12]3[N:11]([C:31](=[O:32])[CH2:30][N:29]3[C:28](=[O:34])[C:27]4=[CH:35][CH:36]=[CH:37][CH:38]=[C:26]4[C:25]3=[O:39])[C:10]3[CH:19]=[CH:20][CH:21]=[CH:22][C:9]2=3)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 812422H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo-HCID 516892Sodium BicarbonateHCID 70110233HCID 70110233, compound

Product 1

HCID 70110631(3aR*,10aS*)-9-(4-Chlorobenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]-diazepine-10(1H)-oneYield 15%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(3aR*,10aS*)-9-(4-Chlorobenzyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one hydrochloride (426 mg, 1.2 mmol) and phthalimidoacetyl chloride (389 mg, 1.7 mmol) were suspended in toluene (4 mL). The suspension was refluxed for 16 hours. To the reaction mixture was added a saturated aqueous solution of sodium hydrogencarbonate, which was subjected to extraction with chloroform. The extract solution was washed with water and a saturated aqueous solution of sodium hydrogencarbonate, which was dried and subjected to filtration. The filtrate was concentrated under reduced pressure. The concentrate was crystallized from ethanol-hexane to give 91 mg (yield 15%) of the titled compound, m.p. 205°-206° C.

Workup

  1. temperatureThe suspension was refluxed for 16 hours
  2. extractionwas subjected to extraction with chloroform
  3. washThe extract solution was washed with water
  4. dry with materiala saturated aqueous solution of sodium hydrogencarbonate, which was dried
  5. filtrationsubjected to filtration
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe concentrate was crystallized from ethanol-hexane

Sources & evidence

ORD record
ord-3d4c8ad97a3641b393140840f75685c3
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

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