Water → 4-Phenoxybutan-1-amine

HRID 2239553Notes

Reaction equation

HRID 2239553 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][N:12]1C(=O)C2C(=CC=CC=2)C1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN.O.CCOC(C)=O>CCO>[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 9321HydrazineHCID 166375972-(4-Phenoxybutyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 1162404-Phenoxybutan-1-amineYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(4-phenoxybutyl)1H-isoindole-1,3(2H)-dione (10.10 g, 3.27 mmol) and 25% hydrazine solution in water (2.88 ml, 13.10 mmol) in EtOH (30 ml) was warmed at reflux. After 1.5 h, EtOAc was added and the mixture was extracted with brine. The combined aqueous phases were then re-extracted with EtOAc and all the organic phases combined. These were then extracted with 1N HCl, the acidic aqueous phases combined, basified with 2N NaOH and re-extracted into EtOAc before evaporating to dryness to give the title compound (0.411 mg, 67%) as an oil. 1H NMR (500 MHz CDCl3): δ 7.32-2.26 (m, 2H), 6.95 (t, 1H), 4.00 (t, 2H), 2.80 (t, 2H), 1.90-1.82 (m, 2H), 1.68-1.62 (m, 2H).

Workup

  1. temperaturewas warmed
  2. temperatureat reflux
  3. extractionthe mixture was extracted with brine
  4. extractionThe combined aqueous phases were then re-extracted with EtOAc and all the organic phases
  5. extractionThese were then extracted with 1N HCl
  6. extractionre-extracted into EtOAc
  7. custombefore evaporating to dryness

Sources & evidence

ORD record
ord-5a0463fa3062463f95ddabc75286d898
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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