Sodium Hydroxide → 7-(4-Aminobutyl)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 68955Notes

Reaction equation

HRID 68955 reaction equation
O.NN.O=C1C2C(=CC=CC=2)C(=O)[N:6]1[CH2:15][CH2:16][CH2:17][CH2:18][C:19]1[CH:36]=[CH:35][C:22]2[N:23]([CH2:33][CH3:34])[C:24](=[O:32])[C:25]([CH3:31])([CH3:30])[C:26](=[O:29])[N:27]([CH3:28])[C:21]=2[CH:20]=1.[OH-].[Na+]>CO>[NH2:6][CH2:15][CH2:16][CH2:17][CH2:18][C:19]1[CH:36]=[CH:35][C:22]2[N:23]([CH2:33][CH3:34])[C:24](=[O:32])[C:25]([CH3:30])([CH3:31])[C:26](=[O:29])[N:27]([CH3:28])[C:21]=2[CH:20]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 706571637-[4-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)butyl]-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Product 1

HCID 706571287-(4-Aminobutyl)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dioneYield 87.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrazine hydrate (0.5 ml) was added to a methanol solution (60 ml) of 7-[4-(1,3-dioxo-1,3-dihydroisoindol-2-yl)butyl]-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine 2,4-dione (1.93 g). The mixture was stirred for 5.5 hours while heated under reflux. After cooled to room temperature, a 1N-sodium hydroxide aqueous solution was added to the reaction mixture, followed by extraction using ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and condensed under reduced pressure to give the title compound (1.2 g) as a yellow solid.

Workup

  1. temperaturewhile heated
  2. temperatureunder reflux
  3. extractionfollowed by extraction
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate, and condensed under reduced pressure

Sources & evidence

ORD record
ord-8ef643c752ce467c8ffeef8f1a7bc15a
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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