Potassium Iodide → 1,4-dihydro-1-[4-[4-(4-methoxyphenyl)-1-piperazinyl]-phenyl]-4-propyl-5H-tetrazol-5-one

HRID 2106771Notes

Reaction equation

HRID 2106771 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH2:13][CH2:14]Cl)[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.Cl.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:28](=[O:29])[N:27]([CH2:30][CH2:31][CH3:32])[N:26]=[N:25]2)=[CH:20][CH:19]=1.[I-].[K+].C1(O)CCCCC1.C(=O)([O-])O.[Na+]>O>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([N:4]2[CH2:13][CH2:14][N:17]([C:18]3[CH:19]=[CH:20][C:21]([N:24]4[C:28](=[O:29])[N:27]([CH2:30][CH2:31][CH3:32])[N:26]=[N:25]4)=[CH:22][CH:23]=3)[CH2:2][CH2:3]2)=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 7966CyclohexanolHCID 15064N,N-Bis(2-chloroethyl)-4-methoxybenzenamineHCID 516892Sodium BicarbonateHCID 230488541-(4-aminophenyl)-1,4-dihydro-4-propyl-5H-tetrazol-5-one monohydrochloride

Product 1

HCID 151254871,4-dihydro-1-[4-[4-(4-methoxyphenyl)-1-piperazinyl]-phenyl]-4-propyl-5H-tetrazol-5-oneYield 39%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 25 parts of N,N-bis(2-chloroethyl)-4-methoxybenzenamine, 25.5 parts of 1-(4-aminophenyl)-1,4-dihydro-4-propyl-5H-tetrazol-5-one monohydrochloride, 2 parts of potassium iodide and 200 parts of cyclohexanol was stirred and refluxed for 5 hours using a water-separator. The reaction mixture was cooled and neutralized with a sodium hydrogen carbonate solution. The product was filtered off and crystallized from 1-butanol, yielding 15.5 parts (39%) of 1,4-dihydro-1-[4-[4-(4-methoxyphenyl)-1-piperazinyl]-phenyl]-4-propyl-5H-tetrazol-5-one; mp. 189.7 ° C. (int. 33).

Workup

  1. temperaturerefluxed for 5 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe product was filtered off
  4. customcrystallized from 1-butanol

Sources & evidence

ORD record
ord-42b8aece752e48ff905e522bbec02a29
Source dataset
uspto-grants-1990_06
Patent number
US04931444

Reaction notes

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