Ammonia → Ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-aminopentanoate

HRID 1980346Notes

Reaction equation

HRID 1980346 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:25]=[CH:24][C:6]([O:7][C:8]2[CH:23]=[CH:22][C:11]([O:12][CH:13]([CH3:21])[CH:14]=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[NH3:28]>C(O)C>[F:1][C:2]([F:26])([F:27])[C:3]1[CH:4]=[CH:5][C:6]([O:7][C:8]2[CH:23]=[CH:22][C:11]([O:12][CH:13]([CH3:21])[CH:14]([NH2:28])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][CH:9]=2)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 156921Ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-2-pentenoate

Product 1

HCID 13477880Ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-aminopentanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-2-pentenoate (0.8 g) in ethanol (25 ml), chilled in an ice bath and under nitrogen, ammonia is flowed over for about 10 minutes while stirring. Reaction is allowed to warm to R.T. The reaction is again chilled and additional ammonia added for about 15 minutes. Reaction is allowed to rise to R.T. and stirring continued over night. Reaction is concentrated under vacuum to an oil. The oily concentrate is purified by prep. thin layer chromatography using ethyl acetate/hexane (1:1) to give ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-aminopentanoate (purity 93.7%, structure confirmed by MS).

Workup

  1. customis flowed over for about 10 minutes
  2. customReaction
  3. temperatureThe reaction is again chilled
  4. customReaction
  5. customto rise to R.T.
  6. stirringstirring
  7. waitcontinued over night
  8. customReaction
  9. concentrationis concentrated under vacuum to an oil
  10. concentrationThe oily concentrate
  11. customis purified by prep

Sources & evidence

ORD record
ord-671fbd5f7cd54f809848e3a92cd9f457
Source dataset
uspto-grants-1985_04
Patent number
US04508906

Reaction notes

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