5-Methoxytryptamine → N-(2-(5-Methoxy-1H-indol-3-yl)ethyl)-3-propoxybenzylamine

HRID 1666873Notes

Reaction equation

HRID 1666873 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=O)[CH2:2][CH3:3].[CH3:13][O:14][C:15]1[CH:26]=[C:25]2[C:18]([NH:19][CH:20]=[C:21]2[CH2:22][CH2:23][NH2:24])=[CH:17][CH:16]=1.[BH4-].[Na+]>CCO>[CH3:13][O:14][C:15]1[CH:26]=[C:25]2[C:18](=[CH:17][CH:16]=1)[NH:19][CH:20]=[C:21]2[CH2:22][CH2:23][NH:24][CH2:8][C:7]1[CH:10]=[CH:11][CH:12]=[C:5]([O:4][CH2:1][CH2:2][CH3:3])[CH:6]=1

Participants

5

Reactant 3

HCID 18335-MethoxytryptamineHCID 27604693-PropoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 21071638N-(2-(5-Methoxy-1H-indol-3-yl)ethyl)-3-propoxybenzylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combine 3-propoxybenzaldehyde (14.05 g, 0.0856 mole) and 5-methoxytryptamine (13.64 g, 0.0717 mole) in 390 mL absolute EtOH. Add molecular sieves (19.2 g) and heat the suspension to reflux. After 4 hours, cool to room temperature and add NaBH4 (37.32 g, 0.2146 mole) in 3 portions. Stir the mixture for 1 hour at room temperature, filter, evaporate the filtrate to a mass of about 100 g, add water and dichloromethane. After separation, wash the aqueous phase with dichloromethane, combine the organic layers, dry over MgSO4, filter, evaporate the solvent in vacuo to afford the title compound.

Workup

  1. additionAdd molecular sieves (19.2 g)
  2. temperatureheat the suspension
  3. temperatureto reflux
  4. filtrationfilter
  5. customevaporate the filtrate to a mass of about 100 g
  6. additionadd water and dichloromethane
  7. customAfter separation
  8. washwash the aqueous phase with dichloromethane
  9. dry with materialdry over MgSO4
  10. filtrationfilter
  11. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-0a5791ecc79d437dae38270f46d2be2f
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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