Sodium Azide → HCID 178420457, compound

HRID 839779

Reaction equation

HRID 839779 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]1([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]#[N:20])[CH2:13][CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl.N1CCOCC1>N1CCOCC1>[C:5]1([N:11]2[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][C:19]3[NH:20][N:3]=[N:2][N:1]=3)[CH2:15][CH2:16]2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 197884Morpholine, hydrochloride (1:1)HCID 2583093-(4-Phenylpiperazin-1-yl)propanenitrile

Product 1

HCID 178420457HCID 178420457, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8083MorpholineSolvent

Procedure

Sodium azide (65 g; 1.0 mol), 4-phenyl-1-(2-cyanoethyl)-piperazine (215 g; 1.0 mol), and morpholine hydrochloride (124 g; 1.0 mol) were dissolved in 1 liter of morpholine, and heated at 120°-125° C with stirring for 4 hours. After the reaction mixture was allowed to cool to room temperature, it was filtered, and the solvent was removed in vacuo. The residue was mixed in water, and the pH of the resulting solution was adjusted to 5. Crude 5-[(4-phenyl-1-piperazyl)ethyl]tetrazole was collected by filtration and was dried; yield -- 170 g. The crude product was recrystallized from water and dried; yield -- 155 g (60% yield; m.p. 190°-194° C).

Workup

  1. temperatureheated at 120°-125° C
  2. filtrationit was filtered
  3. customthe solvent was removed in vacuo
  4. additionThe residue was mixed in water
  5. filtrationCrude 5-[(4-phenyl-1-piperazyl)ethyl]tetrazole was collected by filtration
  6. customwas dried
  7. customThe crude product was recrystallized from water
  8. customdried

Sources & evidence

ORD record
ord-5592581d8e494062af45e3245fc2fc98
Source dataset
uspto-grants-1978_06
Patent number
US04097479

Linked notes

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