Water → 2-(2,3-Dihydro-1H-indol-3-yl)ethan-1-amine

HRID 2057357Notes

Reaction equation

HRID 2057357 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][NH2:12])=[CH:2]1.B.C1COCC1.O>FC(F)(F)C(O)=O.O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]([CH2:10][CH2:11][NH2:12])[CH2:2]1

Participants

6

Reactant 3

HCID 962WaterHCID 1150TryptamineHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 126552512-(2,3-Dihydro-1H-indol-3-yl)ethan-1-amine

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(3-Indolyl)ethylamine in an amount of 9.4 grams (58.8 millimoles) was dissolved in 120 milliliters of trifluoroacetic acid under nitrogen. The solution was cooled in an ice bath and 100 milliliters of about 1 M BH3.THF in tetrahydrofuran solution was added slowly over about 30 minutes. Thereafter, water (50 milliliters) was added, the resulting solution stirred at room temperature for about 75 minutes, and then evaporated in vacuo to about 40 milliliters of a semi-solid viscous oil. The oil was partitioned between methylene chloride and aqueous sodium hydroxide solution (pH>10). The organic layer was dried over potassium carbonate, filtered and evaporated in vacuo to obtain 8.6 grams of a yellow oily 2-(3-indolinyl)ethylamine product of 98 percent purity (by gas layer chromatographic analysis) in a 90 percent isolated yield. NMR was appropriate for the compound. The HCl salt of 2-(3-indolinyl)ethylamine had a melting point of 186°-188° C.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. customevaporated in vacuo to about 40 milliliters of a semi-solid viscous oil
  3. customThe oil was partitioned between methylene chloride and aqueous sodium hydroxide solution (pH>10)
  4. dry with materialThe organic layer was dried over potassium carbonate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-a3a27e4f03304bd283980f4e4e073c16
Source dataset
uspto-grants-1980_07
Patent number
US04210590

Reaction notes

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