1-Butanol → Acetate

HRID 1389166Notes

Reaction equation

HRID 1389166 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)[N:3]=1.Cl.N1CCC(O[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH2:31][C:32]([OH:34])=[O:33])CC1.C([N:37]([CH2:40][CH3:41])[CH2:38][CH3:39])C.[CH2:42]([OH:46])CCC>>[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:37]2[CH2:38][CH2:39][CH:42]([O:46][CH:31]([C:32]([OH:34])=[O:33])[C:26]3[CH:25]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:41][CH2:40]2)[N:3]=1.[C:32]([O-:34])(=[O:33])[CH3:31]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 8471TriethylamineHCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 70579775HCID 70579775, compound

Product 2

HCID 175AcetateHCID 20298097HCID 20298097, compound

Procedure

4-Amino-2-chloro-6,7-dimethoxyquinazoline (4.8 g), 2-(piperidin-4-oxy)phenylacetic acid hydrochloride (4.9 g) and triethylamine (5 ml) in n-butanol (100 ml) were heated under reflux for 20 hours. The mixture was cooled, and the precipitated solid was collected and washed with ether. A sample of this solid (0.7 g) was recrystallised from acetic acid, and the resulting solid washed with ether to give 4-amino-2-[4-(1-carboxy-1-phenyl-methoxy)piperidino]-6,7-dimethoxyquinazoline, acetate (0.56 g), m.p. 271°-274°.

Workup

  1. temperatureunder reflux for 20 hours
  2. temperatureThe mixture was cooled
  3. customthe precipitated solid was collected
  4. washwashed with ether
  5. customA sample of this solid (0.7 g) was recrystallised from acetic acid
  6. washthe resulting solid washed with ether

Sources & evidence

ORD record
ord-b36ae5688ef54caabd30c710ea11c206
Source dataset
uspto-grants-1981_01
Patent number
US04243666

Reaction notes

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