Hydrazine hydrate (1:1) → HCID 20138905, compound

HRID 280145Notes

Reaction equation

HRID 280145 reaction equation
O.NN.C1(=O)[N:8]([CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:14]=2[CH2:15][CH2:16][CH2:17][CH:18]3[N:23]([CH3:25])[CH3:24])C(=O)C2=CC=CC=C12>C(O)C>[NH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH2:15][CH2:16][CH2:17][CH:18]2[N:23]([CH3:24])[CH3:25]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 20138894HCID 20138894, compound

Product 1

HCID 20138905HCID 20138905, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.4 ml of 99% hydrazine hydrate are added to a stirred solution of 5-(3-phthalimidopropoxy)-1-dimethylamino-1,2,3,4-tetrahydronaphthalene (26.8 g prepared in the preceding step) in absolute ethanol (270 ml). The reaction mixture is stirred and heated to reflux for 3 hours, allowed to cool, filtered and the filtrate evaporated in vacuo. The yellow residue is triturated in 5% HCl (250 ml), the suspension filtered and the solid washed with 5% HCl. The clear yellow filtrate is extracted with diethyl ether. The aqueous acidic layer is made strongly alkaline with 50% NaOH solution, resulting in an oily precipitate which is extracted with diethyl ether. The combined organic extracts are dried over sodium sulfate, filtered and the filtrate evaporated in vacuo, yielding 14.7 g of a light yellow oil identified by NMR as the desired 3-aminopropoxy compound.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. temperatureto cool
  4. filtrationfiltered
  5. customthe filtrate evaporated in vacuo
  6. customThe yellow residue is triturated in 5% HCl (250 ml)
  7. filtrationthe suspension filtered
  8. washthe solid washed with 5% HCl
  9. extractionThe clear yellow filtrate is extracted with diethyl ether
  10. customresulting in an oily precipitate which
  11. extractionis extracted with diethyl ether
  12. dry with materialThe combined organic extracts are dried over sodium sulfate
  13. filtrationfiltered
  14. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-1e26be26fd884e43bad6c0ff7b8082db
Source dataset
uspto-grants-1986_05
Patent number
US04588719

Reaction notes

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