Trifluoroacetic acid → 2-(4-Chloro-phenyl)-2-methoxy-ethylamine

HRID 510782Notes

Reaction equation

HRID 510782 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:18][CH3:19])[CH2:9][NH:10]C(=O)OC(C)(C)C)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([O:18][CH3:19])[CH2:9][NH2:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67080810HCID 67080810, compound

Product 1

HCID 532762402-(4-Chloro-phenyl)-2-methoxy-ethylamineYield 84.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(4-chlorophenyl)-2-methoxyethylcarbamate (0.129 g, 0.451 mmol) in dichloromethane (5 ml) was added trifluoroacetic acid (5 ml), and the reaction was stirred at ambient temperature for 16 hours. The reaction was concentrated and taken up in water. Sodium hydroxide (1M) was added until the pH was >13. The mixture was extracted twice with dichloromethane, and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated to yield 71 mg of the title compound (84.7% yield).

Workup

  1. concentrationThe reaction was concentrated
  2. additionSodium hydroxide (1M) was added until the pH was >13
  3. extractionThe mixture was extracted twice with dichloromethane
  4. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e29c56efd0204573833a91eb166dfd9c
Source dataset
uspto-grants-2015_08
Patent number
US09096567B2

Reaction notes

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