Potassium Hydroxide → 2-[(4-Fluorophenethyl)oxy]ethylamine

HRID 613748Notes

Reaction equation

HRID 613748 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][CH2:11][CH2:12][NH:13]C(=O)OC)=[CH:4][CH:3]=1.[OH-].[K+].O.NN>C(O)CO.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][O:10][CH2:11][CH2:12][NH2:13])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 18779044Methyl N-[2-(2-(4-fluorophenyl)ethoxy)ethyl]carbamate

Product 1

HCID 187790642-[(4-Fluorophenethyl)oxy]ethylamine

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Procedure

The product of step d) (8.0 g) was dissolved in ethylene glycol and to this was added potassium hydroxide (48 g) and hydrazine hydrate (8.3 ml). The stirred mixture was heated to 140° for 4 hours then allowed to cool to room temperature overnight. The mixture was then diluted with water and extracted with diethyl ether (×3). The combined organic extracts were washed with brine, dried (MgOS4) and filtered. The volatiles were removed in vacuo to give the subtitle compound (5.36 g).

Workup

  1. temperatureThe stirred mixture was heated to 140° for 4 hours
  2. extractionextracted with diethyl ether (×3)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgOS4)
  5. filtrationfiltered
  6. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-c23dbf51e3e34da2b62ea41f3c4e8157
Source dataset
uspto-grants-1999_12
Patent number
US06008365

Reaction notes

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