Hydrazine → 2-(Benzyloxy)ethanamine

HRID 1396285Notes

Reaction equation

HRID 1396285 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][N:11]1C(=O)C2C(=CC=CC=2)C1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN>C(O)C>[CH2:1]([O:8][CH2:9][CH2:10][NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 14103203HCID 14103203, compound

Product 1

HCID 5338682-(Benzyloxy)ethanamineYield 75.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 127 (10 g, 35 mmol) in ethanol (200 mL) was treated with hydrazine (84 g, 71 mmol, 80% in water) at reflux for 12 hours. After a filtration, the filtrate was concentrated under vacuum to give a residue, which was purified by a silica gel column, eluted with 5% methanol in dichloromethane to afford 128 as light yellow oil (4 g, 74%). (ES, m/z) [M+H]+ 152.0; 1H NMR (300 MHz, CDCl3) δ 7.28-7.40 (m, 5H), 4.56 (s, 2H), 3.54 (t, J=5.4 Hz, 2H), 2.94 (t, J=5.1 Hz, 2H).

Workup

  1. temperatureat reflux for 12 hours
  2. filtrationAfter a filtration
  3. concentrationthe filtrate was concentrated under vacuum
  4. customto give a residue, which
  5. customwas purified by a silica gel column
  6. washeluted with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-de8164f1b44e4594b750b9ab35339da1
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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