Dibenzylamine → (3aR*,10aS*)-9-Benzyl-4-((N,N-dibenzylamino)acetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]-diazepin-10(1H)-one

HRID 356176Notes

Reaction equation

HRID 356176 reaction equation
[CH2:1]([N:8]1[C:14](=[O:15])[C@H:13]2[CH2:16][CH2:17][CH2:18][C@H:12]2[N:11]([C:19](=[O:22])[CH2:20]Cl)[C:10]2[CH:23]=[CH:24][CH:25]=[CH:26][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:27]([NH:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])O.[Na+]>ClCCCl>[CH2:1]([N:8]1[C:14](=[O:15])[C@H:13]2[CH2:16][CH2:17][CH2:18][C@H:12]2[N:11]([C:19](=[O:22])[CH2:20][N:34]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:10]2[CH:23]=[CH:24][CH:25]=[CH:26][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7656DibenzylamineHCID 516892Sodium BicarbonateHCID 70110192(3aR*,10aS*)-9-Benzyl-4-(chloroacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

Product 1

HCID 70113393(3aR*,10aS*)-9-Benzyl-4-((N,N-dibenzylamino)acetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]-diazepin-10(1H)-oneYield 28%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of (3aR*,10aS*)-9-benzyl-4-(chloroacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]-cyclopenta[e][1,4]diazepin-10(1H)-one (1.0 g, 2.7 mmol) and dibenzylamine (5.36 g, 27.1 mmol) in 1,2-dichloroethane (30 mL) was refluxed for 17 hours, to which was added a saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with dichloromethane. The extract solution was washed with water and dried, followed by distilling off the solvent. The residue was purified by silica-gel column chromatography (ethyl acetate-hexane 1:1) to give 0.40 g (yield 28%) as an oily product.

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. washThe extract solution was washed with water
  3. customdried
  4. distillationby distilling off the solvent
  5. customThe residue was purified by silica-gel column chromatography (ethyl acetate-hexane 1:1)
  6. customto give 0.40 g (yield 28%) as an oily product

Sources & evidence

ORD record
ord-56677744fd8e4e3a8493479f049a9d40
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

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