Hydrochloric Acid → HCID 20351353, compound

HRID 1448953Notes

Reaction equation

HRID 1448953 reaction equation
[CH2:1]([N:5]=[C:6]=[O:7])[CH2:2][CH2:3][CH3:4].[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:19]=1[O:20][CH3:21])[N:16]=[CH:15][N:14]=[C:13]2[N:22]1[CH2:27][CH2:26][CH:25]([CH2:28][NH2:29])[CH2:24][CH2:23]1.Cl>C(Cl)(Cl)Cl>[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:19]=1[O:20][CH3:21])[N:16]=[CH:15][N:14]=[C:13]2[N:22]1[CH2:27][CH2:26][CH:25]([CH2:28][NH:29][C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])=[O:7])[CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8110Butyl isocyanateHCID 138818461-(6,7-Dimethoxy-4-quinazolinyl)-4-piperidinemethanamine

Product 1

HCID 20351353HCID 20351353, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

n-Butylisocyanate (1.8 g.) was added to a stirred solution of 6,7-dimethoxy-4-[4-(aminomethyl)piperidino]- quinazoline (5 g.) in dry chloroform (100 ml.). The mixture was then stirred at room temperature for 3 hours, then left standing for 72 hours. An equal volume of 1 N hydrochloric acid was added, the organic phase separated, and the aqueous phase basified to pH 10 with aqueous potassium carbonate solution. The mixture was extracted with chloroform (2×100 ml.), the extracts combined, dried (MgSO4), and taken to dryness in vacuo. The resultant solid was recrystallized twice from acetonitrile and then once from a mixture of isopropanol and ether to yield 6,7-dimethoxy-4-[4-(3-n-butylureidomethyl) piperidino]quinazoline (3.3 g.), m.p. 141°-143° C.

Workup

  1. waitleft
  2. waitstanding for 72 hours
  3. customthe organic phase separated
  4. extractionThe mixture was extracted with chloroform (2×100 ml.)
  5. dry with materialdried (MgSO4)
  6. customThe resultant solid was recrystallized twice from acetonitrile
  7. additiononce from a mixture of isopropanol and ether

Sources & evidence

ORD record
ord-e246fd00f9ee477eb9a21c184d445910
Source dataset
uspto-grants-1980_02
Patent number
US04188391

Reaction notes

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