Sodium Carbonate → 8-[1-(4-Amino-6,7,8-trimethoxy-2-quinazolinyl)-4-piperidinyl]-8-azaspiro[4,5]decan-7,9-dione monohydrochloride

HRID 127276

Reaction equation

HRID 127276 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([O:16][CH3:17])[C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([Cl:18])[N:3]=1.[NH:19]1[CH2:24][CH2:23][CH:22]([N:25]2[C:34](=[O:35])[CH2:33][C:28]3([CH2:32][CH2:31][CH2:30][CH2:29]3)[CH2:27][C:26]2=[O:36])[CH2:21][CH2:20]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[ClH:18].[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([O:16][CH3:17])[C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:19]2[CH2:24][CH2:23][CH:22]([N:25]3[C:26](=[O:36])[CH2:27][C:28]4([CH2:32][CH2:31][CH2:30][CH2:29]4)[CH2:33][C:34]3=[O:35])[CH2:21][CH2:20]2)[N:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 30158042-Chloro-6,7,8-trimethoxyquinazolin-4-amineHCID 128225538-(4-Piperidinyl)-8-azaspiro[4,5]decan-7,9-dione

Product 1

HCID 205562478-[1-(4-Amino-6,7,8-trimethoxy-2-quinazolinyl)-4-piperidinyl]-8-azaspiro[4,5]decan-7,9-dione monohydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture of 5.39 g of 4-amino-2-chloro-6,7,8-trimethoxyquinazoline, 5.25 g of 8-(4-piperidinyl)-8-azaspiro-[4,5]decan-7,9-dione, 4.24 g of anhydrouus sodium carbonate and 75 ml of dimethylformamide is stirred at 150° for 8 hours. After cooling to room temperature it is filtered, the filtrate evaporated, the residue dissolved in ethyl acetate and the solution washed with aqueous sodium bicarbonate and water. It is dried, evaporated, the residue dissolved in 75 ml of ethyl acetate and allowed to crystallize. The crystals are dissolved in 50 ml of hot isopropanol and the solution acidified with hydrogen chloride to pH=1 and the precipitate filtered off, to yield the 8-[1-(4-amino-6,7,8-trimethoxy-2-quinazolinyl)-4-piperidinyl]-8-azaspiro[4,5]decan-7,9dione monohydrochloride melting at 225°-227°.

Workup

  1. filtrationis filtered
  2. customthe filtrate evaporated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washthe solution washed with aqueous sodium bicarbonate and water
  5. customIt is dried
  6. customevaporated
  7. dissolutionthe residue dissolved in 75 ml of ethyl acetate
  8. customto crystallize
  9. dissolutionThe crystals are dissolved in 50 ml of hot isopropanol
  10. filtrationthe precipitate filtered off

Sources & evidence

ORD record
ord-2cf195942baf4d168b10694f110acb88
Source dataset
uspto-grants-1981_03
Patent number
US04255429

Linked notes

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