Sodium Carbonate → 1-[1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-piperidinyl]-4,4-dimethyl-piperidin-2,6-dione monohydrochloride

HRID 1105670Notes

Reaction equation

HRID 1105670 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([Cl:16])[N:3]=1.[CH3:17][C:18]1([CH3:32])[CH2:23][C:22](=[O:24])[N:21]([CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[C:20](=[O:31])[CH2:19]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[ClH:16].[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:28]2[CH2:29][CH2:30][CH:25]([N:21]3[C:20](=[O:31])[CH2:19][C:18]([CH3:17])([CH3:32])[CH2:23][C:22]3=[O:24])[CH2:26][CH2:27]2)[N:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 128225624,4-Dimethyl[1,4'-bipiperidine]-2,6-dione

Product 1

HCID 205562601-[1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-piperidinyl]-4,4-dimethyl-piperidin-2,6-dione monohydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture of 4.79 g of 4-amino-2-chloro-6,7-dimethoxyquinazoline, 4.49 g of 4,4-dimethyl-1-(4-piperidinyl)-piperidin-2,6-dione, 4.24 g of anhydrous sodium carbonate and 75 ml of dimethylformamide is stirred at 150° under nitrogen for 6 hours. It is filtered, the filtrate evaporated, the residue dissolved in ethyl acetate and the solution washed with aqueous sodium carbonate and water. It is dried, evaporated, the residue triturated with isopropanol, filtered off and discarded. The filtrate is made strongly acidic with hydrogen chloride, the precipitate filtered off and triturated with 175 ml of boiling methanol, to yield the 1-[1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-piperidinyl]-4,4-dimethyl-piperidin-2,6-dione monohydrochloride, melting at 279°-280° with decomposition.

Workup

  1. filtrationIt is filtered
  2. customthe filtrate evaporated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washthe solution washed with aqueous sodium carbonate and water
  5. customIt is dried
  6. customevaporated
  7. customthe residue triturated with isopropanol
  8. filtrationfiltered off
  9. filtrationthe precipitate filtered off
  10. customtriturated with 175 ml of boiling methanol

Sources & evidence

ORD record
ord-4e7f4266fb774eecab3ae5d3f9c7f231
Source dataset
uspto-grants-1982_01
Patent number
US04309541

Reaction notes

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