Hydrazine hydrate (1:1) → 1-Amino-3-{3-[(piperidin-1-yl)methyl]phenoxy}propan-2-ol

HRID 1979695Notes

Reaction equation

HRID 1979695 reaction equation
[OH:1][CH:2]([CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH:18]=1)[CH2:3][N:4]1C(=O)C2C(=CC=CC=2)C1=O.O.NN>C(O)C>[NH2:4][CH2:3][CH:2]([OH:1])[CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH:18]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 134690342-[2-Hydroxy-3-[3-(1-piperidinylmethyl)phenoxy]propyl]-1H-isoindole-1,3-(2H)-dione

Product 1

HCID 131898251-Amino-3-{3-[(piperidin-1-yl)methyl]phenoxy}propan-2-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-[2-hydroxy-3-[3-(1-piperidinylmethyl) phenoxy]propyl]-1H-isoindole-1,3-(2H) dione (17.6 g) and hydrazine hydrate (2.5 g) in ethanol (60 ml) was heated under reflux for 3 h. The resulting mixture was evaporated to a solid residue which was suspended in 1N hydrochloric acid (30 ml) and filtered. The filtrate was basified with an excess of potassium carbonate and extracted with isopropanol (3×40 ml). The isopropanol extracts were dried (Na2CO3) and evaporated to a gum which was chromatographed using System A. Crystallisation of the product from n-hexane:ether (20:1) gave the title compound as colourless grains (7.7 g), m.p. 74°-76.5°.

Workup

  1. temperatureunder reflux for 3 h
  2. customThe resulting mixture was evaporated to a solid residue which
  3. filtrationfiltered
  4. extractionextracted with isopropanol (3×40 ml)
  5. dry with materialThe isopropanol extracts were dried (Na2CO3)
  6. customevaporated to a gum which
  7. customwas chromatographed
  8. customCrystallisation of the product from n-hexane:ether (20:1)

Sources & evidence

ORD record
ord-14b99fe09ec644dc888fd98b25a53162
Source dataset
uspto-grants-1984_11
Patent number
US04482552

Reaction notes

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