Trifluoroacetic acid → 4-(4-Chlorophenyl)cyclohexan-1-amine

HRID 1021525Notes

Reaction equation

HRID 1021525 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH:11]([NH:14]C(=O)OC(C)(C)C)[CH2:10][CH2:9]2)=[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]2[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67080532[4-(4-Chloro-phenyl)-cyclohexyl]-carbamic acid tert-butyl ester

Product 1

HCID 37154404-(4-Chlorophenyl)cyclohexan-1-amineYield 72.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(4-chlorophenyl)cyclohexylcarbamate (0.760 g, 2.45 mmol) in dichloromethane (5 ml) was added trifluoroacetic acid (5 ml), and the reaction was stirred at ambient temperature for 2 hours. The reaction was concentrated, taken up in water, and 1M NaOH was added until the pH was >13. The aqueous layer was extracted twice with dichloromethane, and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated to yield 371 mg of the title compound (72.1% yield).

Workup

  1. concentrationThe reaction was concentrated
  2. addition1M NaOH was added until the pH was >13
  3. extractionThe aqueous layer 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-7f8a3ed53ba64223a63ba7112b6d6e86
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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