Sec-Butylamine → HCID 19881217, compound

HRID 1979724Notes

Reaction equation

HRID 1979724 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]1=[CH:15][C:16]([Cl:20])=[N:17][C:18](=[O:19])[N:8]1[CH2:7][CH2:6]2.[CH:21]([NH2:25])([CH2:23][CH3:24])[CH3:22]>CN(C)C=O>[ClH:20].[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]1=[CH:15][C:16]([NH:25][CH:21]([CH2:23][CH3:24])[CH3:22])=[N:17][C:18](=[O:19])[N:8]1[CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 24874Sec-ButylamineHCID 46787202-Chloro-6,7-dihydro-9,10-dimethoxy-4H-pyrimido[6,1-a]isoquinolin-4-one

Product 1

HCID 19881217HCID 19881217, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 9,10-dimethoxy-6,7-dihydro-2-chloro-4H-pyrimido(6,1-a)isoquinolin-4-one (2.5 g), sec-butylamine (10 ml) and dimethylformamide (2 ml) is heated under reflux for 5 hours. The solvent and excess amine are distilled under reduced pressure. The residue is treated with water. A white solid precicipitates and is collected by filtration. The precipitate is crystallized from methylene chloride-ether mixture, yield 2.10 g. The crystals are dissolved in dichloromethane and treated with a solution of etheral hydrochloric acid. The hydrochloride is crystallized from ethanol-ether mixture, m.p. 218°-225° C.

Workup

  1. temperatureunder reflux for 5 hours
  2. distillationThe solvent and excess amine are distilled under reduced pressure
  3. additionThe residue is treated with water
  4. filtrationA white solid precicipitates and is collected by filtration
  5. customThe precipitate is crystallized from methylene chloride-ether mixture, yield 2.10 g
  6. dissolutionThe crystals are dissolved in dichloromethane
  7. additiontreated with a solution of etheral hydrochloric acid
  8. customThe hydrochloride is crystallized from ethanol-ether mixture, m.p. 218°-225° C.

Sources & evidence

ORD record
ord-7b5c5137f3ed41b1ba5c163f9f840914
Source dataset
uspto-grants-1984_11
Patent number
US04482556

Reaction notes

Loading…