Hydrazine hydrate (1:1) → HCID 20138908, compound

HRID 1905727Notes

Reaction equation

HRID 1905727 reaction equation
[OH2:1].NN.C1(=O)N([C:9]2([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][CH2:10]2)C(=O)C2=CC=CC=C12>C(O)C>[NH2:19][CH2:9][CH2:10][CH2:11][O:1][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[CH2:12][CH2:11][CH2:10][CH:9]2[N:19]1[CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86740788HCID 86740788, compound

Product 1

HCID 20138908HCID 20138908, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

85% hydrazine hydrate (8.3 ml) is added to a stirred solution of the phthalimido pyrrolidinyl tetrahydronaphthalene obtained in the previous step (about 51 g) dissolved in absolute ethanol (500 ml), and the reaction mixture is heated to reflux for 3 hours and then allowed to cool. A precipitate forms upon cooling, and the reaction mixture is filtered, the precipitate washed with absolute ethanol, and the filtrate evaporated in vacuo, resulting in a solid. The solid is triturated with 5% aqueous HCl, filtered, and the solid washed with additional 5% HCl solution. The acidic filtrate is washed with diethyl ether and made basic with 50% aqueous sodium hydroxide, resulting in the formation of a golden oil. The oil is extracted with diethyl ether, washed with H2O, dried over sodium sulfate, filtered and evaporated in vacuo, resulting in 17 g of a golden oil. NMR analysis indicates that this oil is the desired amino product.

Workup

  1. customobtained in the previous step (about 51 g)
  2. temperaturethe reaction mixture is heated
  3. temperatureto reflux for 3 hours
  4. temperatureto cool
  5. temperatureA precipitate forms upon cooling
  6. filtrationthe reaction mixture is filtered
  7. washthe precipitate washed with absolute ethanol
  8. customthe filtrate evaporated in vacuo
  9. customresulting in a solid
  10. customThe solid is triturated with 5% aqueous HCl
  11. filtrationfiltered
  12. washthe solid washed with additional 5% HCl solution
  13. washThe acidic filtrate is washed with diethyl ether
  14. customresulting in the formation of a golden oil
  15. extractionThe oil is extracted with diethyl ether
  16. washwashed with H2O
  17. dry with materialdried over sodium sulfate
  18. filtrationfiltered
  19. customevaporated in vacuo

Sources & evidence

ORD record
ord-640878b4f96f4d1792e24d1bdc01326f
Source dataset
uspto-grants-1987_03
Patent number
US04647559

Reaction notes

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