Sodium Sulfate → HCID 52950556, compound

HRID 1880619Notes

Reaction equation

HRID 1880619 reaction equation
C(O[C:6](=O)[NH:7][CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[NH:23][CH:22]=[CH:21]3)[CH2:10][CH2:9]1)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[NH:23]1[C:24]2[C:20](=[CH:19][C:18]([N:11]3[C:12]4[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:8]([NH:7][CH3:6])[CH2:9][CH2:10]3)=[CH:26][CH:25]=2)[CH:21]=[CH:22]1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 67215878HCID 67215878, compound

Product 1

HCID 52950556HCID 52950556, compoundYield 5.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

[1-(1H-Indol-5-yl)-1,2,3,4-tetrahydro-quinolin-4-yl]-carbamic acid tert-butyl ester (1.2 g, 4.3 mmol) was dissolved in 30 mL THF and the mixture was cooled to 0° C. Lithium aluminum hydride (0.70 g, 4.6 mmol) suspended in 5 mL THF was added, and the mixture was warmed to room temperature with stirring, and then heated to reflux for three hours. The mixture was cooled room temperature, diluted with THF (25 mL), and then cooled to 0° C. Hydrous sodium sulfate (36 g) was slowly added with stirring, and the mixture was stirred for 30 minutes, then filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by flash chromatography (methylene chloride/methanol/ammonium hydroxide 90:9:1) to give 0.064 g of [1-(1H-indol-5-yl)-1,2,3,4-tetrahydro-quinolin-4-yl]-methyl-amine, MS (M+H)=278.

Workup

  1. additionwas added
  2. temperaturethe mixture was warmed to room temperature
  3. temperatureheated
  4. temperatureto reflux for three hours
  5. temperatureThe mixture was cooled room temperature
  6. temperaturecooled to 0° C
  7. stirringwith stirring
  8. stirringthe mixture was stirred for 30 minutes
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customthe resulting residue was purified by flash chromatography (methylene chloride/methanol/ammonium hydroxide 90:9:1)

Sources & evidence

ORD record
ord-df081f8443804b26950f146afd516462
Source dataset
uspto-grants-2012_11
Patent number
US08318770B2

Reaction notes

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