Hydrochloric Acid → 7-Amino-1-(1-piperazinyl)-naphthalene

HRID 235151Notes

Reaction equation

HRID 235151 reaction equation
C([NH:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[CH:15][CH:16]=[C:17]2[N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:12][CH:11]=1)(=O)C1C=CC=CC=1.Cl>C(O)C>[NH2:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[CH:15][CH:16]=[C:17]2[N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 189675377-Benzamido-1-(1-piperazinyl)-naphthalene2×

Product 1

HCID 189675327-Amino-1-(1-piperazinyl)-naphthaleneYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product of Example 11 (7-benzamido-1-(1-piperazinyl)-naphthalene, (0.063 g, 0.19 mmol) was combined with hydrochloric acid in ethanol (4 mL) and refluxed 16 hours. The reaction was concentrated at reduced pressure and the residue was neutralized with 4 N sodium hydroxide and extracted with methylene chloride. The organic phase was washed with brine, dried and concentrated to a tan solid (0.041 g). The solid was recrystallized from ethyl acetate/hexane to give 0.020 g (47%) of the title compound as light tan crystals. mp 184°-186° C. HRMS m/e calculated for C14H17N3 : 227.1419. Observed m/e 227.1405.

Workup

  1. temperaturerefluxed 16 hours
  2. concentrationThe reaction was concentrated at reduced pressure
  3. extractionextracted with methylene chloride
  4. washThe organic phase was washed with brine
  5. customdried
  6. concentrationconcentrated to a tan solid (0.041 g)
  7. customThe solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-ba7fe15075624f5d973b232c3674cecf
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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