Water → 7-(Benzyloxycarbonylamino)-1-(4-methyl--piperazinyl)-naphthalene

HRID 235123Notes

Reaction equation

HRID 235123 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21].C(=O)([O-])[O-].[K+].[K+].O>C(Cl)Cl>[CH2:23]([O:22][C:20]([NH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1)=[O:21])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformate2×HCID 11430Potassium CarbonateHCID 233534847-Amino-1-(4-methyl-1-piperazinyl)-naphthalene

Product 1

HCID 189675227-(Benzyloxycarbonylamino)-1-(4-methyl--piperazinyl)-naphthaleneYield 82.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

7-Amino-1-(4-methyl-1-piperazinyl)-naphthalene (0.225 g, 0.933 mmol), benzyl chloroformate (0.147 mL, 1.03 mmol), and potassium carbonate (0.142 g, 1.03 mmol) were combined in a two phase mixture of methylene chloride (10 mL) and water (3 mL) and the mixture was stirred at room temperature overnight. Benzyl chloroformate (0.147 mL, 1.03 mmol) was added and the reaction was stirred 5 hours more. The reaction was diluted with methylene chloride and the phases were separated. The organic layer was washed with brine, dried over calcium sulfate and concentrated to a brown oil which was flash chromatographed on silica gel (1×4 inches). Gradient elution with ethyl acetate/hexane of from 50% to 100% followed by gradient ethanol/ethyl acetate elution of from 5% to 10% gave 0.29 g of a brown foam. This residue was recrystallized from ethyl acetate to give 0.095 g (27%) of the title product in two crops; mp 143°-144° C. Analysis calculated for C23H25N3O2 : C, 73.58; H, 6.71; N, 11.19. Found: C, 73.46; H, 6.71; N, 11.05.

Workup

  1. stirringthe reaction was stirred 5 hours more
  2. customthe phases were separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried over calcium sulfate
  5. concentrationconcentrated to a brown oil which
  6. customchromatographed on silica gel (1×4 inches)
  7. washGradient elution with ethyl acetate/hexane of from 50% to 100%
  8. washfollowed by gradient ethanol/ethyl acetate elution of from 5% to 10%

Sources & evidence

ORD record
ord-2a7d740eed1d42f6beb4f3a6a1b4da71
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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