Hydrochloric Acid → 3-[[2-(diethylamino)ethoxy]methyl]-4H-pyrimido[2,1-a]isoquinolin-4-one dihydrochloride

HRID 543287Notes

Reaction equation

HRID 543287 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]1[C:18](=[O:19])[N:9]2[CH:10]=[CH:11][C:12]3[C:17]([C:8]2=[N:7][CH:6]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3.[CH2:20]([N:22]([CH2:25][CH2:26][Cl:27])[CH2:23][CH3:24])[CH3:21].[ClH:28]>CN(C)C=O.C(OCC)C>[ClH:27].[ClH:28].[CH2:20]([N:22]([CH2:25][CH3:26])[CH2:23][CH2:24][O:3][CH2:4][C:5]1[C:18](=[O:19])[N:9]2[CH:10]=[CH:11][C:12]3[C:17]([C:8]2=[N:7][CH:6]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH3:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 13364Diethylaminoethyl chlorideHCID 24758Sodium hydrideHCID 138510983-(hydroxymethyl)-4H-pyrimido[2,1-a]isoquinolin-4-one

Product 1

HCID 202061183-[[2-(diethylamino)ethoxy]methyl]-4H-pyrimido[2,1-a]isoquinolin-4-one dihydrochlorideYield 28%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

To 0.7 g of sodium hydride (14.5 mmol) stirred in 40 ml of dry dimethylformamide under nitrogen was added dropwise over a 15 minute period a solution of 2.0 g of 3-(hydroxymethyl)-4H-pyrimido[2,1-a]isoquinolin-4-one (8.3 mmol) in 40 ml of warm dimethylformamide. After stirring for 1 hour, 1.58 g of diethylaminoethyl chloride (11.6 mmol) was added dropwise over a 15 minute period. The reaction mixture was stirred for 3 hours, then poured onto ice-water and extracted 3 times with 500 ml of methylene chloride. The extracts were dried and concentrated in vacuo to yield a semi-solid, to which 15 ml of isopropanolic hydrochloric acid solution and diethyl ether were added. The crystalline solid which formed was collected and washed with ether to yield 3-[[2-(diethylamino)ethoxy]methyl]-4H-pyrimido[2,1-a]isoquinolin-4-one dihydrochloride (0.973 g; 28% yield) of the formula: ##STR24## having a melting point of 128.7° C. and the following elemental analysis:

Workup

  1. stirringThe reaction mixture was stirred for 3 hours
  2. additionpoured onto ice-water
  3. extractionextracted 3 times with 500 ml of methylene chloride
  4. customThe extracts were dried
  5. concentrationconcentrated in vacuo
  6. customto yield a semi-solid
  7. customThe crystalline solid which formed
  8. customwas collected
  9. washwashed with ether

Sources & evidence

ORD record
ord-23e25acc009a4699be8d469e32e3e344
Source dataset
uspto-grants-1987_04
Patent number
US04661592

Reaction notes

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