Hydrogen chloride-ethyl acetate → 4-(Adamantan-1-yl)aniline

HRID 1626771Notes

Reaction equation

HRID 1626771 reaction equation
[C:1]12([C:11]3[CH:16]=[CH:15][C:14]([NH:17]C(=O)OC(C)(C)C)=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.Cl.C(OCC)(=O)C>C(OCC)(=O)C>[C:1]12([C:11]3[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=3)[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86661495Tert-butyl [4-(adamantan-1-yl)phenyl]carbamate

Product 1

HCID 5985444-(Adamantan-1-yl)aniline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4 mL of ethyl acetate was added to 678 mg (2.07 mmol) of tert-butyl [4-(adamantan-1-yl)phenyl]carbamate, and then 4 mL of 4N hydrogen chloride/ethyl acetate was added at 0° C. The mixture was stirred at room temperature for 10 hours. The solvent was distilled off under reduced pressure, and ethyl acetate was added to the residue. The resultant was washed with an aqueous sodium hydrogen carbonate solution and saturated saline in this order, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, thereby quantitatively giving 4-(adamantan-1-yl)aniline.

Workup

  1. distillationThe solvent was distilled off under reduced pressure, and ethyl acetate
  2. additionwas added to the residue
  3. washThe resultant was washed with an aqueous sodium hydrogen carbonate solution and saturated saline in this order
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a8615193e2504af5b3227815d39d4cb8
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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