Sodium Hydroxide → 2-(2,3-Dihydro-3-methylindol-2-yl)ethylamine

HRID 1646752Notes

Reaction equation

HRID 1646752 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[CH2:11][CH2:12][NH2:13].C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C>[CH3:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]1[CH2:11][CH2:12][NH2:13]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydride2×HCID 118195262-(3-methyl-1H-indol-2-yl)ethan-1-amine

Product 1

HCID 197871342-(2,3-Dihydro-3-methylindol-2-yl)ethylamineYield 71.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2-(3-methylindol-2-yl)ethylamine (2.5 g) in acetic acid [25 ml) at 15° C. was added sodium cyanoborohydride (1.62 g) in one portion. The solution was stirred at room temperature. After 3 hours, sodium cyanoborohydride (1.0 g) was added and the mixture was stirred at room temperature for 12 hours. After dilution with ice-water, the reaction mixture was made basic with sodium hydroxide pellets and extracted three times with ether. The ether layer was washed with water and brine, dried over anhydrous sodium sulfate, and evaporated in vacuo to give 2-(2,3-dihydro-3-methylindol-2-yl)ethylamine (1.80 g) as an oil. The oil was used in the next reaction without further purification.

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. extractionextracted three times with ether
  3. washThe ether layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-58b307ec625f41af83488d3485ba2991
Source dataset
uspto-grants-1993_01
Patent number
US05180728

Reaction notes

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