Hydrazine hydrate (1:1) → 2-Hydroxy-3-[3-(1-piperidylmethyl)benzyloxy]propylamine

HRID 542781Notes

Reaction equation

HRID 542781 reaction equation
[OH:1][CH:2]([CH2:15][O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:19]=1)[CH2:3][N:4]1C(=O)C2C(=CC=CC=2)C1=O.O.NN>C(O)C>[OH:1][CH:2]([CH2:15][O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:19]=1)[CH2:3][NH2:4]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 135354762-[2-Hydroxy-3-[3-(1-piperidylmethyl)benzyloxy]propyl]-1H-isoindole-1,3-dione

Product 1

HCID 135354772-Hydroxy-3-[3-(1-piperidylmethyl)benzyloxy]propylamineYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8.60 g (0.021 mol) of 2-[2-hydroxy-3-[3-(1-piperidylmethyl)benzyloxy]propyl]-1H-isoindole-1,3-dione and 3.3 ml of hydrazine hydrate (80%) are boiled in 80 ml of ethanol for 3 hours. The residue left after concentration of the mixture by evaporation is taken up in 50 ml of water; 8 ml of conc. hydrochloric acid are added and the reaction mixture is filtered. The filtrate is adjusted to pH 12 with conc. sodium hydroxide solution and extracted with 3×40 ml methylene chloride. The organic phase is dehydrated with Na2SO4 and concentrated by evaporation under vacuum. The residue is distilled in a high vacuum. 4.44 g (76%) of a colourless oil, boiling point 145°-155° C./1×10-2 mbar, are obtained.

Workup

  1. waitThe residue left after concentration of the mixture
  2. customby evaporation
  3. addition8 ml of conc. hydrochloric acid are added
  4. filtrationthe reaction mixture is filtered
  5. extractionextracted with 3×40 ml methylene chloride
  6. concentrationconcentrated by evaporation under vacuum
  7. distillationThe residue is distilled in a high vacuum

Sources & evidence

ORD record
ord-a6aae7bdcba946859dd30476f332638c
Source dataset
uspto-grants-1987_04
Patent number
US04659721

Reaction notes

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