Hydrochloric Acid → 7-(Benzylamino)-1-(4-methyl-1-piperazinyl)-naphthalene

HRID 235118Notes

Reaction equation

HRID 235118 reaction equation
[C:1]([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)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CSC.B.Cl.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:1]([NH:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[CH:15][CH:16]=[C:17]2[N:20]2[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]2)=[CH:12][CH:11]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 99611507-Benzamido-1-(4-methyl-1-piperazinyl)-naphthaleneHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 233534717-(Benzylamino)-1-(4-methyl-1-piperazinyl)-naphthaleneYield 45.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title product of example 1 (0.12 g, 0.348 mmol) was dissolved in toluene (4 mL) and borane-dimethyl sulfide (0.3 mL, 3 mmol) was added. The mixture was refluxed 3 hours and cooled. 6N HCl and ethyl acetate were added and the mixture was refluxed until all the solids had dissolved. The organic phase was separated and discarded. The aqueous phase was made basic with 4N NaOH and extracted with methylene chloride. This organic phase was washed with brine, dried over calcium sulfate and concentrated. The crude product was purified by flash chromatography on silica gel (0.5×4 inches). Elution with 50% and then 75% ethyl acetate/hexane gave 0.053 g of product. This material was further purified by trituration with hexane to provide 0.03 g, (26%) of the title product as a tan powder: mp 115°-117° C.; 1H NMR δ 7.64 (d, J=8.5 Hz, 1H), 7.46-7.24 (m, 6H), 7.14 (t, J=7.5 Hz, 1H), 7.0 (d, J=2.5 Hz, 1H), 7.00 (ss, J=1, 7.5 Hz, 1H), 6.94 (dd, J=2.5, 8.5 Hz, 1H), 4.50 (br s, 2H), 4.34 (br m, 1H), 3.01 (br s, 4H), 2.53 (br s, 4H), 2.38 (s, 3H). Analysis calculated for C22H25N3 ·0.5 H2O: C, 77.61; H, 7.70; N, 12.34. Found: C, 77.78; H, 7.48; N, 12.07.

Workup

  1. temperatureThe mixture was refluxed 3 hours
  2. temperaturecooled
  3. temperaturethe mixture was refluxed until all the solids
  4. dissolutionhad dissolved
  5. customThe organic phase was separated
  6. extractionextracted with methylene chloride
  7. washThis organic phase was washed with brine
  8. dry with materialdried over calcium sulfate
  9. concentrationconcentrated
  10. customThe crude product was purified by flash chromatography on silica gel (0.5×4 inches)
  11. washElution with 50%

Sources & evidence

ORD record
ord-a825d80424f04e2287191428195038e1
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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