Triethylamine hydrochloride → HCID 178419813, compound

HRID 394580Notes

Reaction equation

HRID 394580 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)#[N:2].Cl.C(N(CC)CC)C.[N-:20]=[N+:21]=[N-:22].[Na+]>COCCOC>[NH:20]1[C:1]([C:3]2[CH:4]=[C:5]3[C:9](=[CH:10][CH:11]=2)[NH:8][CH:7]=[CH:6]3)=[N:2][N:22]=[N:21]1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 27513Indole-5-carbonitrileHCID 33557Sodium Azide

Product 1

HCID 178419813HCID 178419813, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 5-cyano-1H-indole (88 g), triethylamine hydrochloride (225 g), and sodium azide (150 g) was heated in 1,2-dimethoxyethane (DME) at reflux temperature for 48 hours. The solvent was evaporated in vaciio and the residue was dissolved in ethyl acetate (500 mL) and water (500 mL). pH was adjusted to 10 by addition of concentrated aqueous NaOH solution. The aqueous phase was separated and pH was adjusted to 4 by addition of acetic acid. The precipitated crystalline title compound 1a was filtered off and subsequently dried in vacuo. Yield 82 g, mp 205° C.

Workup

  1. temperatureat reflux temperature for 48 hours
  2. customThe solvent was evaporated in vaciio
  3. dissolutionthe residue was dissolved in ethyl acetate (500 mL)
  4. additionpH was adjusted to 10 by addition of concentrated aqueous NaOH solution
  5. customThe aqueous phase was separated
  6. additionpH was adjusted to 4 by addition of acetic acid
  7. filtrationThe precipitated crystalline title compound 1a was filtered off
  8. customsubsequently dried in vacuo

Sources & evidence

ORD record
ord-4ce5b9e924ca4bf3bf32a758793d8aa8
Source dataset
uspto-grants-2003_08
Patent number
US06602889B1

Reaction notes

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