Formaldehyde → 1H-Indole-3-methanamine, 5-ethyl-N,N-dimethyl-

HRID 1394022Notes

Reaction equation

HRID 1394022 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)[CH3:2].Cl.[CH3:13][NH:14][CH3:15].[CH2:16]=O>C(O)(C)C>[CH2:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:13][N:14]([CH3:16])[CH3:15])[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 123992105-Ethyl-1H-indole

Product 1

HCID 2696951H-Indole-3-methanamine, 5-ethyl-N,N-dimethyl-Yield 97%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

5-Ethylindole 10 (1.0 g, 6.89 mmol) was combined with isopropyl alcohol (200 mL), N,N-dimethylamine hydro chloride (718 mg, 6.95 mmol) and aqueous formaldehyde (37%, 589 mg, 6.95 mmol) and heated at reflux for 2 hours. The reaction mixture was allowed to cool to room temperature, the solvent was evaporated and the resulting residue was dissolved in EtOAc and washed with saturated NaHCO3. The organic layer was dried over MgSO4, filtered and evaporated to give compound 11 as a solid in (1.35 g for a 97% yield; M+1=203.2)

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. customthe solvent was evaporated
  4. dissolutionthe resulting residue was dissolved in EtOAc
  5. washwashed with saturated NaHCO3
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-bfe2c4a9740643b8912a94e68c74025d
Source dataset
uspto-grants-2008_03
Patent number
US07348338B2

Reaction notes

Loading…