Hydrazine hydrate (1:1) → Tzb-30878

HRID 1714772Notes

Reaction equation

HRID 1714772 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]([NH:23][C:24]2[CH2:29][CH2:28][CH2:27][CH2:26][C:25]=2[C:30]([O:32]CC)=O)=O)[CH2:13][CH2:12]1.O.[NH2:36][NH2:37]>C(O)C>[NH2:36][N:37]1[C:30](=[O:32])[C:25]2[CH2:26][CH2:27][CH2:28][CH2:29][C:24]=2[N:23]=[C:21]1[CH2:20][CH2:19][CH2:18][CH2:17][N:14]1[CH2:13][CH2:12][N:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 23155633Ethyl 2-[5-(4-quinolin-2-ylpiperazin-1-yl)pentanoylamino]cyclohex-1-enecarboxylate

Product 1

HCID 11430418Tzb-30878Yield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 120 ml of ethanol, 8.0 g of ethyl 2-[5-(4-quinolin-2-ylpiperazin-1-yl)pentanoylamino]cyclohex-1-enecarboxylate as synthesized in above Step 4-1-C was dissolved, and to the solution 60 ml of hydrazine monohydrate was added, followed by 4 hours' heating under reflux. Distilling the solvent off under reduced pressure, the residue was dissolved in chloroform, washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. Distilling the solvent off under reduced pressure, the residue was purified on silica gel column chromatography (chloroform:methanol=50:1) to provide 3.8 g (51%) of 3-amino-2-[4-(4-quinolin-2-ylpiperazin-1-yl)butyl]-5,6,7,8-tetrahydro-3H-quinazolin-4-one.

Workup

  1. dissolutionwas dissolved
  2. temperature' heating
  3. temperatureunder reflux
  4. distillationDistilling the solvent off under reduced pressure
  5. dissolutionthe residue was dissolved in chloroform
  6. washwashed with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationDistilling the solvent off under reduced pressure
  9. customthe residue was purified on silica gel column chromatography (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-ac9255cad01b4f889e6fcb7de65f0553
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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