Triethylamine → 1-Piperazineethanamine, N-(2,6-dimethyl-3-nitro-4-pyridinyl)-4-(diphenylmethyl)-, trihydrochloride

HRID 414468Notes

Reaction equation

HRID 414468 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][CH2:5]1.[NH2:23][C:24]1[CH:29]=[C:28]([CH3:30])[N:27]=[C:26]([CH3:31])[C:25]=1[N+:32]([O-:34])=[O:33].C(N(CC)CC)C>C(O)(C)C>[ClH:1].[ClH:1].[ClH:1].[CH3:31][C:26]1[C:25]([N+:32]([O-:34])=[O:33])=[C:24]([NH:23][CH2:2][CH2:3][N:4]2[CH2:9][CH2:8][N:7]([CH:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:6][CH2:5]2)[CH:29]=[C:28]([CH3:30])[N:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4741635HCID 4741635, compoundHCID 212809212,6-Dimethyl-3-nitropyridin-4-amine

Product 1

HCID 30666161-Piperazineethanamine, N-(2,6-dimethyl-3-nitro-4-pyridinyl)-4-(diphenylmethyl)-, trihydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In accordance with process variant (c), 10 g (0.08 mol) of 1-(2-chloroethyl)-4-diphenylmethylpiperazine, 13.4 g (0.08 mol) of 4-amino-2,6-dimethyl-3-nitropyridine and 10 g (0.1 mol) of triethylamine were dissolved in 300 ml of isopropanol in a 500 ml round-bottomed flask, and the solution was heated to boiling for 10 hours. It was then cooled to room temperature, and the precipitate was filtered off with suction. The latter was extracted by stirring with ethyl acetate, and the mixture was filtered and the filtrate was evaporated to dryness. The remaining residue was taken up in ethanol, and ethanolic HCl was added. The solution was evaporated to dryness in vacuo, and the residue was recrystallized from Isopropanol/diisopropyl ethyl (4:1; vol.).

Workup

  1. temperaturethe solution was heated
  2. filtrationthe precipitate was filtered off with suction
  3. extractionThe latter was extracted
  4. filtrationthe mixture was filtered
  5. customthe filtrate was evaporated to dryness
  6. additionethanolic HCl was added
  7. customThe solution was evaporated to dryness in vacuo
  8. customthe residue was recrystallized from Isopropanol/diisopropyl ethyl (4:1; vol.)

Sources & evidence

ORD record
ord-ca4bcac56de44e74a5b551e6db34c9b9
Source dataset
uspto-grants-1988_12
Patent number
US04792554

Reaction notes

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