1H-Indole-3-ethanamine, 4-methoxy- → 2-(4-Methoxy-1H-indol-3-yl)ethan-1-amine--hydrogen chloride (1/1)

HRID 1666815Notes

Reaction equation

HRID 1666815 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:14]=1[C:10]([CH2:11][CH2:12][NH2:13])=[CH:9][NH:8]2.[NH4+].[Cl-:16]>CO>[ClH:16].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:14]=1[C:10]([CH2:11][CH2:12][NH2:13])=[CH:9][NH:8]2

Participants

4

Reactant 2

HCID 192191H-Indole-3-ethanamine, 4-methoxy-HCID 25517Ammonium Chloride

Product 1

HCID 568323902-(4-Methoxy-1H-indol-3-yl)ethan-1-amine--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 4-methoxytryptamine (1 g, 5.26 mmol) in MeOH and add of NH4Cl (0.97 eq, 0.27 g, 5.10 mmol). After 30 minutes, evaporate in vacuo to remove the MeOH leaving a thick orange oil. Dissolve the oil in MeOH and add dropwise to Et2O (200 mL) with vigorous stirring giving a gummy white precipitate. Stir with heating to give the title compound as a solid: 1H NMR (d6-DMSO, 300 MHz): 3.06 (bs, 4H); 3.86 (s, 3H); 6.46 (dd, 1H); 7.06-6.9 (m, 3H); 7.93 (bs, 1H); 10.9 (s, 1H); MS (ES+): m/z 191 (M+H)+; 175 (M−CH3)+; 174 (M−NH2)+; (ES−): 189 (M−H)−; Analysis for C11H15ClN2O: Calcd.: C, 58.2788; H, 6.6692; N, 12.3566. found C, 58.18; H, 6.73; N, 12.15.

Workup

  1. customevaporate in vacuo
  2. customto remove the MeOH leaving a thick orange oil
  3. dissolutionDissolve the oil in MeOH
  4. additionadd dropwise to Et2O (200 mL)
  5. customgiving a gummy white precipitate
  6. stirringStir
  7. temperaturewith heating

Sources & evidence

ORD record
ord-c8c31f5fe4bd4336bcc3bae80fdf9040
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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