Tert-butyl 2-(6-chloro-1H-indol-3-YL)ethylcarbamate → [2-(6-Chloro-1h-indol-3-yl)ethyl](methyl)amine

HRID 1371851Notes

Reaction equation

HRID 1371851 reaction equation
C(O[C:6]([NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=O)(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:6][NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[NH:13][CH:12]=1

Participants

4

Reactant 2

HCID 21071680Tert-butyl 2-(6-chloro-1H-indol-3-YL)ethylcarbamateHCID 21226445Aluminium lithium hydride

Product 1

HCID 21071655[2-(6-Chloro-1h-indol-3-yl)ethyl](methyl)amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Combine N-t-butoxycarbonyl-2-(6-chloro-1H-indol-3-yl)ethylamine (1.3 g, 4.41 mmol) and dry THF (20 ml) and add dropwise to an ice bath cooled suspension of LiAlH4 (1.0 g, 26.5 mmol) in dry THF (30 ml). Heat to reflux. After 2 hours, cool to ambient temperature and stir. After 15 hours, quench with saturated NaSO4 (100 ml/mol), stir for 1 hour at ambient temperature, then filter under vacuum. Wash precipitate with THF and evaporated filtrate and washes to residue. Chromatograph the residue on silica gel eluting with dichloromethane/2N NH3(methanol) (84/16) to give the title compound: MS (ACPI): m/e 209.0 (M+1).

Workup

  1. temperaturecooled
  2. temperatureHeat to reflux
  3. waitAfter 15 hours
  4. customquench with saturated NaSO4 (100 ml/mol)
  5. stirringstir for 1 hour at ambient temperature
  6. filtrationfilter under vacuum
  7. washWash precipitate with THF
  8. customevaporated filtrate and washes to residue

Sources & evidence

ORD record
ord-decce43b52604d12a185ddb3434cde8c
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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