2-Isopropylcyclohexan-1-one → 8-Isopropyl-5,6,7,8-tetrahydro-quinazoline

HRID 1042400Notes

Reaction equation

HRID 1042400 reaction equation
[CH:1]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=O)([CH3:3])[CH3:2].[C:11](O)(=O)C.[CH:15]([NH2:17])=[NH:16]>C(O)CCC>[CH:1]([CH:4]1[C:5]2[N:17]=[CH:15][N:16]=[CH:11][C:6]=2[CH2:7][CH2:8][CH2:9]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 704902-Isopropylcyclohexan-1-oneHCID 160693Formamidine acetate

Product 1

HCID 587529058-Isopropyl-5,6,7,8-tetrahydro-quinazolineYield 40.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

A 100 mL reaction flask is charged with 2-isopropyl-cyclohexanone (10 g, 0.07 mol), formamidine acetate (40 g, 0.4 mol), and butanol (50 mL). The reaction mixture is heated to 130° C. and stirred for 24 hours. The crude mass is washed once with aqueous sulfuric acid (10%, 100 mL) followed by twice with brine (30 mL). Butanol is recovered by roto-evaporation. The crude product is further purified with liquid chromatography (Biotage® system) and then crystallized. Product 8-isopropyl-5,6,7,8-tetrahydro-quinazoline (˜5 g) is obtained.

Workup

  1. customA 100 mL reaction flask
  2. washThe crude mass is washed once with aqueous sulfuric acid (10%, 100 mL)
  3. customButanol is recovered by roto-evaporation
  4. customThe crude product is further purified with liquid chromatography (Biotage® system)
  5. customcrystallized

Sources & evidence

ORD record
ord-ac3db79d78a9403fb74c69012f50fa6d
Source dataset
uspto-grants-2013_10
Patent number
US08557876B2

Reaction notes

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