Water → 3-(2-Aminoethyl)-7-nitro-1,2,4,5-tetrahydro-3H-3-benzazepine

HRID 329373Notes

Reaction equation

HRID 329373 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([CH2:23][CH2:24][N:25]1[CH2:31][CH2:30][C:29]2[CH:32]=[CH:33][C:34]([N+:36]([O-:38])=[O:37])=[CH:35][C:28]=2[CH2:27][CH2:26]1)=[N+]=[N-].O>O1CCCC1>[NH2:20][CH2:23][CH2:24][N:25]1[CH2:31][CH2:30][C:29]2[CH:32]=[CH:33][C:34]([N+:36]([O-:38])=[O:37])=[CH:35][C:28]=2[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 19872046HCID 19872046, compound

Product 1

HCID 198720493-(2-Aminoethyl)-7-nitro-1,2,4,5-tetrahydro-3H-3-benzazepine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (0.71 g) was added to a solution of 3-(2-azidoethyl)-7-nitro-1,2,4,5-tetrahydro-3H-3-benzazepine (0.68 g) in dry tetrahydrofuran under a nitrogen atmosphere and the reaction mixture was then stirred at room temperature for 18 hours and heated at 50° for 5 hours. After cooling, water was added and the mixture was stirred at room temperature for 3 days. The solvent was then evaporated in vacuo and the residue was diluted with 2M hydrochloric acid and washed three times with ethyl acetate. The aqueous layer was made alkaline (pH=12) with 5M sodium hydroxide and extracted three times with ethyl acetate. The latter organic extracts were combined and dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as an oil, yield 0.56 g, which was used without further purification.

Workup

  1. temperatureheated at 50° for 5 hours
  2. temperatureAfter cooling
  3. stirringthe mixture was stirred at room temperature for 3 days
  4. customThe solvent was then evaporated in vacuo
  5. additionthe residue was diluted with 2M hydrochloric acid
  6. washwashed three times with ethyl acetate
  7. extractionextracted three times with ethyl acetate
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-12844719546c44c1a697218e673769bc
Source dataset
uspto-grants-1990_01
Patent number
US04891372

Reaction notes

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