Sodium Hydroxide → 3-(3-dimethylaminopropyl)-4,5,6,7-tetrahydro-1H-indole

HRID 1836121

Reaction equation

HRID 1836121 reaction equation
[CH3:1][N:2]([CH3:17])[C:3](=O)[CH2:4][CH2:5][C:6]1[C:14]2[C:13](=O)[CH2:12][CH2:11][CH2:10][C:9]=2[NH:8][CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.O>[CH3:17][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]1[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[NH:8][CH:7]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 22571143HCID 22571143, compound

Product 1

HCID 111484413-(3-dimethylaminopropyl)-4,5,6,7-tetrahydro-1H-indoleYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

N,N-Dimethyl-3-(4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionamide (8 g, 0.034 mol) was suspended in 125 ml of tetrahydrofuran and lithium aluminum hydride (5.2 g, 0.136 mol) was slowly added. The mixture was refluxed over night, cooled in ice, and 5 ml of water and then 5 ml of 15% sodium hydroxide solution was slowly added. The mixture was stirred for 45 minutes. Water (15 ml) and sodium sulfate were added and the mixture filtered to remove solids. The solids were washed with ethyl acetate and the filtrate was concentrated to give dimethyl-[3-(4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-amine (6.3 g, 90% yield).

Workup

  1. temperatureThe mixture was refluxed over night
  2. temperaturecooled in ice
  3. filtrationthe mixture filtered
  4. customto remove solids
  5. washThe solids were washed with ethyl acetate
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-57587fae93fd4b91a63c9f8689843fe9
Source dataset
uspto-grants-2004_08
Patent number
US06777417B2

Linked notes

Loading…