Ethylamine → HCID 13646217, compound

HRID 979499Notes

Reaction equation

HRID 979499 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]1[N:19]([CH2:20][CH2:21]Cl)[C:18](=[O:23])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1.[CH2:24]([NH2:26])[CH3:25].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]1[N:19]([CH2:20][CH2:21][NH:26][CH2:24][CH3:25])[C:18](=[O:23])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1

Participants

5

Reactant 3

HCID 6341EthylamineHCID 11430Potassium CarbonateHCID 13646088HCID 13646088, compound

Product 1

HCID 13646217HCID 13646217, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 328 mg (1 mmol) of 2-(2-methoxyphenylmethyl) -3-(2-chloroethyl)-4(3H)-quinazolinone and a 70% aqueous ethylamine solution (0.6 ml) in ethanol (10 ml) was heated at 80 ° C. W for 8 hours in a sealed tube. The solvent was distilled off under reduced pressure and to the residue thus obtained there was added a 10 % aqueous potassium carbonate solution, followed by extraction with dichloromethane. The thus obtained dichloromethane solution was dried over magnesium sulfate and then concentrated. The resulting residue was purified by silica gel column chromatography (eluent: 1% ethanol-chloroform) to obtain 55 mg (16%) of 2-(2-methoxyphenylmethyl)-3-(2-ethylaminoethyl)-4(3H)-quinazolinone as an oily substance. Subsequently, the thus obtained quinazolinone was dissolved in ether (3 ml) and to the resulting solution was added a 10% HCl/ethanol solution. The precipitated crystals were collected by filtration to obtain the hydrochride of the captioned compound.

Workup

  1. distillationThe solvent was distilled off under reduced pressure and to the residue
  2. customthus obtained there
  3. extractionfollowed by extraction with dichloromethane
  4. dry with materialThe thus obtained dichloromethane solution was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was purified by silica gel column chromatography (eluent: 1% ethanol-chloroform)

Sources & evidence

ORD record
ord-e798369bbaaf4d908d8c2ab6f7bb3124
Source dataset
uspto-grants-1987_05
Patent number
US04668682

Reaction notes

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