Dimethylamine → N,N-Dimethyltryptamine

HRID 1844251Notes

Reaction equation

HRID 1844251 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[CH3:13][NH:14][CH3:15].C(=O)(O)[O-].[Na+].CO>C(O)(=O)C>[NH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([CH2:3][CH2:2][N:14]([CH3:15])[CH3:13])=[CH:5]1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 887MethanolHCID 769243-(2-Bromoethyl)indoleHCID 516892Sodium Bicarbonate

Product 1

HCID 6089N,N-Dimethyltryptamine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 250 mg of 3-(2-bromoethyl)indole in a round-bottomed flask, a 10 M excess of dimethylamine (6 mL of 2M in MeOH) was added and the solution was stirred at r.t. overnight. After adding 5 mL sodium bicarbonate (2%), the reaction mixture was extracted with chloroform (3×5 ml) and back extracted with H2O (1×5 mL). The combined extracts were dried over MgSO4 and evaporation of the solvent gave the product in crystalline form. Yield: 0.21 g, 84%, yellowish crystals. m.p.: 45-47° C.; TLC (EtAc:MeOH:acetic acid, 8:2:0.5 v/v/v): RF=0.33. 1H NMR, δ: 10.43 (s, 1H), 7.42-7.06 (m, 5H), 2.68 (m, 4H), 2.26 (S, 6H). 13C NMR (CDCl3): δ 136.5, 124.3, 123.2, 121.2, 119.7, 117.6, 113.4, 111.1, 61.7, 41.2, 22.4. Anal. calcd for C12H16N2: C, 76.55; H, 8.57; N, 14.88%. Found; C, 76.60; H, 8.70; N, 14.70%.

Workup

  1. extractionthe reaction mixture was extracted with chloroform (3×5 ml)
  2. extractionback extracted with H2O (1×5 mL)
  3. dry with materialThe combined extracts were dried over MgSO4 and evaporation of the solvent
  4. customgave the product in crystalline form

Sources & evidence

ORD record
ord-68fe65e3152a43158607d4766b14be51
Source dataset
uspto-grants-2015_02
Patent number
US08946302B2

Reaction notes

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