N,N-Dimethyl-1,3-propanediamine → HCID 13646117, compound

HRID 979496Notes

Reaction equation

HRID 979496 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH2:11][C:12]1[O:17][C:16](=O)[C:15]2[CH:19]=[C:20]([O:23][CH:24]([CH3:26])[CH3:25])[CH:21]=[CH:22][C:14]=2[N:13]=1.[CH3:27][N:28]([CH3:33])[CH2:29][CH2:30][CH2:31][NH2:32]>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH2:11][C:12]1[N:32]([CH2:31][CH2:30][CH2:29][N:28]([CH3:33])[CH3:27])[C:16](=[O:17])[C:15]2[C:14](=[CH:22][CH:21]=[C:20]([O:23][CH:24]([CH3:26])[CH3:25])[CH:19]=2)[N:13]=1

Participants

4

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 13646085HCID 13646085, compound

Product 1

HCID 13646117HCID 13646117, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2.84 g (8 mmol) of 2-(2,5-dimethoxyphenylmethyl)-6-isopropoxy-4H-3,1-benzoxazin-4-one and 0.82 g (8 mmol) of 3-dimethylaminopropylamine were heated under reflux for 15 hours in xylene (20 ml). After the xylene was distilled off, the residue obtained was purified by silica gel column chromatography (eluent; 2% ethanol/chloroform) to obtain 1.46 g (42%) of 2-(2,5-dimethoxyphenylmethyl)-3-(3-dimethylaminopropyl)-6-isopropoxy-4(3H)-quinazolinone as an oily substance. Subsequently, 0.22 g of the 2-(2,5-dimethoxyphenylmethyl)-3-(3-dimethylaminopropyl)-6-isopropoxy-4(3H)-quinazolnone was dissolved in ether (15 ml) and to the resulting soluion, there was added an ethanolic solution containing 0.07 g (0.6 mmol) of maleic acid. The thus obtained solution was allowed to stand for one day. The precipitated colorless crystals were collected by filtration to obtain 0.25 g of the maleate which is the desired compound.

Workup

  1. distillationAfter the xylene was distilled off
  2. customthe residue obtained
  3. customwas purified by silica gel column chromatography (eluent; 2% ethanol/chloroform)

Sources & evidence

ORD record
ord-9699f208bcdf41539bf7260ecf957300
Source dataset
uspto-grants-1987_05
Patent number
US04668682

Reaction notes

Loading…