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Ammonium Chloride → HCID 178420261, compound

HRID 1415155
Notes
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Reaction equation

HRID 1415155 reaction equation
[C:1]1([C:7]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)([CH2:10][CH2:11][N:12]2[CH2:17][CH:16]3[CH2:18][CH2:19][CH:13]2[CH2:14][CH2:15]3)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:26]=[N+:27]=[N-:28].[Na+].[Cl-].[NH4+].[Cl-].[Li+]>CN(C)C=O>[C:1]1([C:7]([C:8]2[NH:28][N:27]=[N:26][N:9]=2)([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH2:10][CH2:11][N:12]2[CH2:17][CH:16]3[CH2:15][CH2:14][CH:13]2[CH2:19][CH2:18]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 433294Lithium ChlorideHCID 203569662-Phenyl-(3-pyridyl)-4-(2-azabicyclo[2.2.2]oct-2-yl)butyronitrile

Product 1

HCID 178420261HCID 178420261, compound

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5.69 parts of 2-phenyl-(3-pyridyl)-4-(2-azabicyclo[2.2.2]oct-2-yl)butyronitrile, 1.67 parts of sodium azide, 1.38 parts of ammonium chloride and 0.025 parts of lithium chloride in 30 parts by volume of dimethylformamide was stirred for 12 hours under nitrogen at 120° C. After the reaction time was completed, the material was cooled and filtered. The collected precipitate was washed with dimethylformamide and water. The precipitate was then dissolved in 100 parts by volume of 0.2N NaOH. The resultant solution was filtered. The filtrates were neutralized with dilute hydrochloric acid. The product which separated was recrystallized from ethanol. The procedure afforded 5-[1-phenyl-1-(3-pyridyl)-3-(2-azabicyclo[2.2.2]oct-2-yl)propyl]-1H-tetrazole.

Workup

  1. temperaturethe material was cooled
  2. filtrationfiltered
  3. washThe collected precipitate was washed with dimethylformamide and water
  4. dissolutionThe precipitate was then dissolved in 100 parts by volume of 0.2N NaOH
  5. filtrationThe resultant solution was filtered
  6. customThe product which separated
  7. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-9b8cbecba36f4c6a9d15d7ab3d618bb4
Source dataset
uspto-grants-1977_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04003904

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes