Water → HCID 178420099, compound

HRID 972550Notes

Reaction equation

HRID 972550 reaction equation
[C:1]1([C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:14][CH2:13]2)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[N-:31]=[N+:32]=[N-:33].[Na+]>CN(C)C=O.[Cl-].[NH4+].[Cl-].[Li+]>[C:1]1([C:7]([C:8]2[NH:33][N:32]=[N:31][N:9]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:14][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 214047972,2-Diphenyl-4-(4-phenylpiperidino)butyronitrile

Product 1

HCID 178420099HCID 178420099, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolventHCID 433294Lithium ChlorideSolvent

Procedure

11.0 Parts of 2,2-diphenyl-4-(4-phenylpiperidino)butyronitrile are dissolved in 55 parts by volume of dimethylformamide along with 2.82 parts of sodium azide, 2.32 parts of ammonium chloride and 0.04 parts of lithium chloride. This mixture is heated under a nitrogen atmosphere, in an oil bath which is kept at 125° C. The solution is cooled and poured into water which caused the formation of a gummy precipitate. The solvent phase is decanted from the gum. The gum is then crystallized from a mixture of methanol-ether and dried in vacuum to provide an off-white solid which is recrystallized from a mixture of methanol-ether and again dried in vacuum to provide 5-[1,1-diphenyl-3-(4-phenylpiperidino)propyl]-1H-tetrazole hemimethanolate, melting at 149° - 157° C. and having the following formula ##STR8##

Workup

  1. temperatureThis mixture is heated under a nitrogen atmosphere, in an oil bath which
  2. customis kept at 125° C
  3. temperatureThe solution is cooled
  4. customThe solvent phase is decanted from the gum
  5. customThe gum is then crystallized from a mixture of methanol-ether
  6. customdried in vacuum
  7. customto provide an off-white solid which
  8. customis recrystallized from a mixture of methanol-ether
  9. customagain dried in vacuum

Sources & evidence

ORD record
ord-b5779c0e6f5340a0a8606def85790994
Source dataset
uspto-grants-1977_10
Patent number
US04053477

Reaction notes

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