Sodium Carbonate → Pyrrolo(3,2-b)(1,5)benzodiazepin-10(1H)-one, 4,9-dihydro-1,3-dimethyl-4-(1-oxo-3-(1-pyrrolidinyl)propyl)-

HRID 1902489

Reaction equation

HRID 1902489 reaction equation
Br[CH2:2][CH2:3][C:4]([N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[NH:10][C:9](=[O:17])[C:8]2[N:18]([CH3:22])[CH:19]=[C:20]([CH3:21])[C:7]1=2)=[O:5].[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[CH3:22][N:18]1[C:8]2[C:9](=[O:17])[NH:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:6]([C:4](=[O:5])[CH2:3][CH2:2][N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[C:7]=2[C:20]([CH3:21])=[CH:19]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 31268PyrrolidineHCID 205154874-(3-Bromopropionyl)-1,3-dimethyl-1,4,9,10-tetrahydropyrrolo[3,2-b][1,5]benzodiazepin-10-one

Product 1

HCID 3068589Pyrrolo(3,2-b)(1,5)benzodiazepin-10(1H)-one, 4,9-dihydro-1,3-dimethyl-4-(1-oxo-3-(1-pyrrolidinyl)propyl)-

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.9 g of 4-(3-bromopropionyl)-1,3-dimethyl-1,4,9,10-tetrahydropyrrolo[3,2-b][1,5]benzodiazepin-10-one and 0.75 g of pyrrolidine are warmed at 80° C. for 4 hours in 50 ml of dioxane. After the solvent has been stripped off in vacuo, the residue is taken up in a little saturated sodium carbonate solution. The mixture is extracted three times with 30 ml of ethyl acetate each time, the combined extracts are dried over sodium sulfate, and the solvent is stripped off in vacuo. The remaining crystalline residue is recrystallized from a little acetonitrile. Yield: 1.5 g of the title compound of m.p. 185° C.

Workup

  1. extractionThe mixture is extracted three times with 30 ml of ethyl acetate each time
  2. dry with materialthe combined extracts are dried over sodium sulfate
  3. customThe remaining crystalline residue is recrystallized from a little acetonitrile

Sources & evidence

ORD record
ord-36598b10d8e1476f948130b2687047ed
Source dataset
uspto-grants-1982_12
Patent number
US04363816

Linked notes

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