Hydrazine hydrate (1:1) → 3-(4-Benzyloxyphenoxy)propylamine

HRID 361717Notes

Reaction equation

HRID 361717 reaction equation
[CH2:1]([O:8][C:9]1[CH:29]=[CH:28][C:12]([O:13][CH2:14][CH2:15][CH2:16][N:17]2C(=O)C3=CC=CC=C3C2=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>C(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH2:14][CH2:15][CH2:16][NH2:17])=[CH:28][CH:29]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13338484N-[3-(4-benzyloxyphenoxy)propyl]phthalimide

Product 1

HCID 283720103-(4-Benzyloxyphenoxy)propylamineYield 58.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-[3-(4-benzyloxyphenoxy)propyl]phthalimide (3.87 g) and hydrazine hydrate (0.55 g) in ethanol (40 ml) was heated at reflux for 3 hours. The reaction mixture was allowed to cool, filtered and the filtrate evaporated. Sodium hydroxide solution (2M, 20 ml) was added to the residue, the aqueous mixture extracted with ethyl acetate and the ethyl acetate extract dried. The solid collected by filtration of the cooled reaction mixture was suspended in sodium hydroxide solution (2M, 20 ml) and extracted with ethyl acetate. The ethyl acetate extract was dried, combined with the dried ethyl acetate derived from the filtrate and the combined extract evaporated to give 3-(4-benzyloxyphenoxy)propylamine as a solid (1.5 g), m.p. 115° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. temperatureto cool
  4. filtrationfiltered
  5. customthe filtrate evaporated
  6. additionSodium hydroxide solution (2M, 20 ml) was added to the residue
  7. extractionthe aqueous mixture extracted with ethyl acetate
  8. extractionthe ethyl acetate extract
  9. customdried
  10. filtrationThe solid collected by filtration of the cooled reaction mixture
  11. extractionextracted with ethyl acetate
  12. extractionThe ethyl acetate extract
  13. customwas dried
  14. extractionthe combined extract
  15. customevaporated

Sources & evidence

ORD record
ord-ca566fe3ae2946d4a6b14346ad88e3a3
Source dataset
uspto-grants-1999_02
Patent number
US05866611

Reaction notes

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