Chloride → N,N,N-Trimethyl-1H-indol-5-aminium chloride

HRID 1798024Notes

Reaction equation

HRID 1798024 reaction equation
[Cl-:1].C1(C([O-])=C([N+]([O-])=O)C=C([N+]([O-])=O)C=1)[N+]([O-])=O.[NH:18]1[C:26]2[C:21](=[CH:22][C:23]([N+:27]([CH3:30])([CH3:29])[CH3:28])=[CH:24][CH:25]=2)[CH:20]=[CH:19]1.CO>C(O)(C)C.CC(C)=O>[Cl-:1].[NH:18]1[C:26]2[C:21](=[CH:22][C:23]([N+:27]([CH3:30])([CH3:29])[CH3:28])=[CH:24][CH:25]=2)[CH:20]=[CH:19]1

Participants

6

Reactant 3

HCID 312ChlorideHCID 887MethanolHCID 86642287HCID 86642287, compound

Product 1

HCID 23281N,N,N-Trimethyl-1H-indol-5-aminium chlorideYield 57%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3776IsopropanolSolvent

Procedure

a mixture of 300 g of a Dowex 2 resin (chloride), 46 g of 5-indolyltrimethylammonium picrate and 1200 mL of 83% methanol is stirred for 17 hours at ambient temperature. The resin is eliminated by filtration and washed with 100 mL of methanol. The filtrate is evaporated under vacuum in order to produce a syrupy residue which is dissolved in 120 mL of warm isopropanol and diluted in 800 mL of acetone. The residue which precipitates is eliminated by decantation and the supernatant is diluted in another 700 mL of acetone. The solution is left for 3 days in order to produce beige crystals which are recovered, washed with acetone and dried in order to produce 13.5 g (57%) of product (melting point: 200-201° C.). The centesimal analysis is described in the publication.

Workup

  1. filtrationThe resin is eliminated by filtration
  2. washwashed with 100 mL of methanol
  3. customThe filtrate is evaporated under vacuum in order
  4. customto produce a syrupy residue which
  5. customThe residue which precipitates
  6. additionthe supernatant is diluted in another 700 mL of acetone
  7. waitThe solution is left for 3 days in order
  8. customto produce beige crystals which
  9. customare recovered
  10. washwashed with acetone
  11. customdried in order

Sources & evidence

ORD record
ord-30cbceae18fa4a88aca7a05f45ecaa47
Source dataset
uspto-grants-2013_01
Patent number
US08343964B2

Reaction notes

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