1,3-Bis(aminomethyl)cyclohexane → (3-Aminomethyl-cyclohexylmethyl)-[2-(2-naphthalen-1-yl-vinyl)-quinazolin-4-yl]-amine

HRID 1171042Notes

Reaction equation

HRID 1171042 reaction equation
Cl[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH:12]=[CH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)[NH:3]1.[NH2:24][CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH:28]([CH2:32][NH2:33])[CH2:27]1>C(O)C>[NH2:24][CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH:28]([CH2:32][NH:33][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([CH:12]=[CH:13][C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=[CH:16][CH:15]=3)[N:3]=2)[CH2:27]1

Participants

4

Reactant 2

HCID 174061,3-Bis(aminomethyl)cyclohexaneHCID 1784783434-Chloro-2-(2-naphthalen-1-yl-vinyl)-3,4-dihydro-quinazoline

Product 1

HCID 68681390(3-Aminomethyl-cyclohexylmethyl)-[2-(2-naphthalen-1-yl-vinyl)-quinazolin-4-yl]-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Chloro-2-(2-naphthalen-1-yl-vinyl)-3,4-dihydro-quinazoline (0.08 mmol), C-(3-aminomethyl-cyclohexyl)-methylamine (0.24 mmol) and 2 ml ethyl alcohol are placed in an 8 ml glass vial sealed with a teflon-lined screw cap. The mixture is heated at 80° for 3 hrs. After cooling to rt, the ethyl alcohol is removed. Ethyl acetate (3 ml) and water (3 ml) are added to the vial. After agitation, the water was removed. The procedure is repeated with water and aq. NaCl (sat.). Purification with silica gel afforded (3-aminomethyl-cyclohexylmethyl)-[2-(2-naphthalen-1-yl-vinyl)-quinazolin-4-yl]-amine;

Workup

  1. customcap
  2. temperatureThe mixture is heated at 80° for 3 hrs
  3. customthe ethyl alcohol is removed
  4. additionEthyl acetate (3 ml) and water (3 ml) are added to the vial
  5. customAfter agitation, the water was removed
  6. customPurification with silica gel

Sources & evidence

ORD record
ord-3e196e30367a4ea7a3fb9a80d5c0c842
Source dataset
uspto-grants-2010_11
Patent number
US07829566B2

Reaction notes

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