Triethylamine → 1-benzyl-4-(1,2,3,4-tetrahydro-2-oxo-3-quinazolinyl)piperidine

HRID 67082Notes

Reaction equation

HRID 67082 reaction equation
Cl.Cl.Cl.[CH2:4]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[NH2:25])[CH2:13][CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(N(CC)CC)C.[C:33](N1C=CN=C1)(N1C=CN=C1)=[O:34]>C(#N)C>[CH2:4]([N:11]1[CH2:12][CH2:13][CH:14]([N:17]2[CH2:18][C:19]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:25][C:33]2=[O:34])[CH2:15][CH2:16]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-Carbonyldiimidazole2×HCID 204971641-Benzyl-4-[N-(o-aminobenzyl)-amino]-piperidine trihydrochloride

Product 1

HCID 130510211-benzyl-4-(1,2,3,4-tetrahydro-2-oxo-3-quinazolinyl)piperidineYield 54.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In this reference example, 4.04 g of 1-benzyl-4-[N-(o-aminobenzyl)-amino]-piperidine trihydrochloride, 3.04 g of triethylamine, 2.03 g of 1,1'-carbonyldiimidazole and 50 ml of acetonitrile are mixed and stirred at room temperature for 4 hours. Then, 0.8 g of 1,1'-carbonyldiimidazole is further added to the mixture and the resultant mixture is refluxed with heating for 20 minutes. The solution is cooled to room temperature. The crystals deposited are separated by filtration, washed with water and dried to obtain 2.50 g of a crude product. The crude product is recrystallized from hot ethanol to obtain 1.75 g of the desired product.

Workup

  1. temperaturewith heating for 20 minutes
  2. temperatureThe solution is cooled to room temperature
  3. customThe crystals deposited are separated by filtration
  4. washwashed with water
  5. customdried
  6. customto obtain 2.50 g of a crude product
  7. customThe crude product is recrystallized from hot ethanol

Sources & evidence

ORD record
ord-c835122ef3424078906fed53e8c23d09
Source dataset
uspto-grants-1982_08
Patent number
US04344948

Reaction notes

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