Diethyl Ether → HCID 68407402, compound

HRID 888009Notes

Reaction equation

HRID 888009 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:30])[C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)=[CH:19][CH:18]=1)=O)(C)(C)C.C(OCC)C>Cl>[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:30])[C:17]1[CH:18]=[CH:19][C:20]([N:23]2[CH2:24][CH2:25][N:26]([CH3:29])[CH2:27][CH2:28]2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 68407704HCID 68407704, compound

Product 1

HCID 68407402HCID 68407402, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

N-(2-t-Butoxycarbonylaminophenyl)-4-(1-methylpiperazin-4-yl)benzamide (Method 16, 196 mg, 0.48 mmol) was dissolved in a 1M solution of hydrogen chloride in diethyl ether (7.2 ml, 7.2 mmol) and stirred at ambient temperature for 24 hours. The resultant precipitate was collected by filtration and washed with diethyl ether. To the solid was added a 2M solution of aqueous sodium hydroxide (5 ml) and the mixture extracted with ethyl acetate. The organic extract was dried over magnesium sulfate, filtered and evaporated to afford the title compound as a colourless solid (16 mg, 11%); NMR Spectrum: (CDCl3) 2.36 (s, 3H), 2.57 (t, 4H), 3.33 (t, 4H), 3.88 (br, 2H), 6.81 (m, 2H), 6.91 (d, 2H) 7.06 (t, 1H), 7.27 (d, 1H), 7.79 (s, 1H), 7.80 (m, 2H); Mass Spectrum: M+H+ 311.

Workup

  1. filtrationThe resultant precipitate was collected by filtration
  2. washwashed with diethyl ether
  3. additionTo the solid was added a 2M solution of aqueous sodium hydroxide (5 ml)
  4. extractionthe mixture extracted with ethyl acetate
  5. extractionThe organic extract
  6. dry with materialwas dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-57549b59efa441a48b8274ca2f4eded9
Source dataset
uspto-grants-2012_08
Patent number
US08247562B2

Reaction notes

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