Ammonium Chloride → HCID 178420776, compound

HRID 1980870Notes

Reaction equation

HRID 1980870 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)#[N:2].[N-:22]=[N+:23]=[N-:24].[Na+].[Cl-].[NH4+].[Cl-].[Li+]>CN(C=O)C>[NH:22]1[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]=2[C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[N:2][N:24]=[N:23]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 433294Lithium ChlorideHCID 204007973-(4-Cyanobutyl)-2-(3-pyridyl)indole

Product 1

HCID 178420776HCID 178420776, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 540 mg of 3-(4-cyanobutyl)-2-(3-pyridyl)indole, 173 mg of sodium azide, 142 mg of ammonium chloride and 5 mg of lithium chloride in 2 ml of DMF is heated at 120° overnight. After cooling the mixture is filtered and the filtrate diluted with ca. 25 ml of water. After the pH is adjusted to 10-11 with 3N NaOH, the solution is washed with ether to remove unreacted nitrile. The aqueous phase is adjusted to pH 5-6 with 2N HCl and extracted with ether. The ether extract is washed with water, dried over MgSO4 and concentrated in vacuo. The residue is purified to give 3-[4-(5-tetrazolyl)-butyl]-2-(3-pyridyl)indole.

Workup

  1. temperatureis heated at 120° overnight
  2. temperatureAfter cooling the mixture
  3. filtrationis filtered
  4. additionthe filtrate diluted with ca. 25 ml of water
  5. washthe solution is washed with ether
  6. customto remove unreacted nitrile
  7. extractionextracted with ether
  8. extractionThe ether extract
  9. washis washed with water
  10. dry with materialdried over MgSO4
  11. concentrationconcentrated in vacuo
  12. customThe residue is purified

Sources & evidence

ORD record
ord-71bf041256fb487f94291c0f4ee4ecc3
Source dataset
uspto-grants-1985_04
Patent number
US04511573

Reaction notes

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