Trifluoroacetic acid → 1-Methyl-1H-indole-3-ethylamine

HRID 1749513Notes

Reaction equation

HRID 1749513 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][CH2:12][NH:13]C(=O)OC(C)(C)C)=[CH:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][CH2:12][NH2:13])=[CH:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71202127Tert-butyl N-[2-(1-methyl-1H-indol-3-YL)ethyl]carbamate

Product 1

HCID 234921-Methyl-1H-indole-3-ethylamineYield 85.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl (2-(1-methyl-1H-indol-3-yl)ethyl)carbamate (1.29 g, 4.71 mmol) in DCM (15 mL) was added TFA (7 mL) at ˜0° C. to 5° C. The resulting reaction mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated to give the crude product which was diluted with DCM and washed with sodium bicarbonate aqueous solution. The organic layer was washed with brine, dried and concentrated to give the desired product (700 mg, 4.02 mmol, 85% yield) as yellow oil. MS (ESI) m/z 175.1 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated
  3. customto give the crude product which
  4. washwashed with sodium bicarbonate aqueous solution
  5. washThe organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5faad02c97c942e18f1d277cdf32f2f7
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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