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

HRID 1741448Notes

Reaction equation

HRID 1741448 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-8c9cdc72e819460ebeca123977705ee5
Source dataset
uspto-grants-1999_10
Patent number
US05973167

Reaction notes

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