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

HRID 1749545Notes

Reaction equation

HRID 1749545 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 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (2-(1-methyl-1H-indol-3-yl)ethyl)carbamate (4 g, 14.6 mmol) in DCM (30 mL) was added TFA (15 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 a crude title compound (2.5 g, crude) as yellow oil. MS (ESI) m/z 175.1 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-190f6711efc94699abbca9fa0472bfd9
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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