Ammonium Chloride → Hydrochloric Acid

HRID 485356Notes

Reaction equation

HRID 485356 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)[N:9]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:8]=1)#[N:2].[N-:22]=[N+:23]=[N-:24].[Na+].[Cl-:26].[NH4+].[Cl-].[Li+]>CN(C)C=O>[ClH:26].[ClH:26].[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)[N:9]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[CH:8]=2)=[N:2][N:24]=[N:23]1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 433294Lithium ChlorideHCID 20270200HCID 20270200, compound

Product 2

HCID 313Hydrochloric AcidHCID 1784782823-[4-(5-tetrazolyl)butyl]-N-(3-pyridyl)indole hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5.16 g of 3-(4-cyanobutyl)-N-(3-pyridyl)indole, 1.88 g of sodium azide, 1.57 g of ammonium chloride and 10 mole % of lithium chloride is heated in 14 ml of dry N,N-dimethylformamide at 125° C. for 17 hours. The reaction mixture is cooled, filtered and evaporated to a residual oil which is partitioned between 50 ml of water and 50 ml of ethyl acetate. The aqueous phase is adjusted to pH=2, extracted with 20 ml of ethyl acetate, adjusted to pH=5 and the resulting solid collected by filtration. Treatment with 6.2 ml of 3N ethereal hydrogen chloride yields 3-[4-(5-tetrazolyl)butyl]-N-(3-pyridyl)indole hydrochloride.

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered
  3. customevaporated to a residual oil which
  4. customis partitioned between 50 ml of water and 50 ml of ethyl acetate
  5. extractionextracted with 20 ml of ethyl acetate
  6. filtrationthe resulting solid collected by filtration

Sources & evidence

ORD record
ord-78dc36a3bfa946a08d6cb92e0159498b
Source dataset
uspto-grants-1985_08
Patent number
US04536505

Reaction notes

Loading…