Ethanol → 7-Amino-1-(4-methyl-1-piperazinyl)-naphthalene

HRID 235110Notes

Reaction equation

HRID 235110 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][N:23]([CH3:26])[CH2:22][CH2:21]2)=[CH:12][CH:11]=1)(=O)C1C=CC=CC=1.C(O)C.[OH-].[Na+]>Cl>[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][N:23]([CH3:26])[CH2:22][CH2:21]2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 99611507-Benzamido-1-(4-methyl-1-piperazinyl)-naphthalene2×

Product 1

HCID 233534847-Amino-1-(4-methyl-1-piperazinyl)-naphthaleneYield 92%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

7-Benzamido-1-(4-methyl-1-piperazinyl)-naphthalene (the product from example 1, 3.75 g, 10.87 mmol) was slurried in 6N HCl (a mixture of concentrated HCl (25 mL) and ethanol (25 mL)) (50 mL) and refluxed for 3.5 hours. The mixture was cooled and brought to pH 10 with 1N sodium hydroxide. The aqueous mixture was extracted with methylene chloride. The organic layer was washed with brine, dried over calcium sulfate and concentrated to afford 2.44 g (92%) of the title product which was suitable for use in further reactions without purification. A sample was recrystallized from isopropyl alcohol for analysis: mp 157°-159° C.; 1H NMR δ 7.65 (d, J=8.5 Hz, 1H), 7.44 (d, J=8 Hz, 1H), 7.35 (d, J=2 Hz, 1H), 7.17 (t, J=8 Hz, 1H), 7.04 (d with long range coupling, J=7 Hz, 1H), 6.94 (dd, J=2.5, 8.5 Hz, 1H), 3.88 (br s, 3H), 3.12 (br s, 4H), 2.42 (s, 3H). Analysis calculated for C15H19N3:C, 74.65; H, 7.94; N, 17.41. Found: C, 74.79; H, 8.14; N, 17.41.

Workup

  1. temperaturerefluxed for 3.5 hours
  2. temperatureThe mixture was cooled
  3. extractionThe aqueous mixture was extracted with methylene chloride
  4. washThe organic layer was washed with brine
  5. dry with materialdried over calcium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7f92f66c0b324e129eed1ebcbaec66a5
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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