Hydrazine hydrate (1:1) → 7-(3-Aminopropoxy)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 1183085Notes

Reaction equation

HRID 1183085 reaction equation
O.NN.O=C1C2C(=CC=CC=2)C(=O)[N:6]1[CH2:15][CH2:16][CH2:17][O: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>CO>[NH2:6][CH2:15][CH2:16][CH2:17][O: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

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 686733627-(3-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)propoxy)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Product 1

HCID 686735217-(3-Aminopropoxy)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dioneYield 77.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrazine hydrate (1.17 ml, 24 mmol) was added to a methanol solution (60 ml) of 7-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)propoxy]-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (2.70 g, 6.0 mmol), and stirred while heating under reflux for 2 hours. The reaction mixture was concentrated under reduced pressure. A 1N-sodium hydroxide aqueous solution was added to the residue, and stirred for 30 minutes, and extraction with dichloromethane was performed. The organic layer was washed with water and a saturated sodium chloride aqueous solution, in this order. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to thereby obtain 1.48 g (yield: 77%) of 7-(3-aminopropoxy)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione as a colorless oil.

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux for 2 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionA 1N-sodium hydroxide aqueous solution was added to the residue
  5. stirringstirred for 30 minutes
  6. extractionextraction with dichloromethane
  7. washThe organic layer was washed with water
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-617ed3722caa47b8967039ad43f18fde
Source dataset
uspto-grants-2014_03
Patent number
US08664217B2

Reaction notes

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