Morpholine → 3,4-Dihydro-2-methyl-4-[2-(4-morpholinyl)ethyl]pyrimido[1.6-a]benzimidazol-1(2H)-one

HRID 973420

Reaction equation

HRID 973420 reaction equation
Cl[CH2:2][CH2:3][CH:4]1[C:9]2=[N:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:8]2[C:7](=[O:17])[N:6]([CH3:18])[CH2:5]1.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>>[CH3:18][N:6]1[CH2:5][CH:4]([CH2:3][CH2:2][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:9]2=[N:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:8]2[C:7]1=[O:17]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 199898454-(2-Chloroethyl)-3,4-dihydro-2-methylpyrimido[1,6-a]benzimidazol-1(2H)-one

Product 1

HCID 199898563,4-Dihydro-2-methyl-4-[2-(4-morpholinyl)ethyl]pyrimido[1.6-a]benzimidazol-1(2H)-one

Conditions

Temperature
60 °C

Procedure

To 20 mL of morpholine was added 3.5 g (0.0133 mol) of 4-(2-chloroethyl)-3,4-dihydro-2-methylpyrimido[1,6-a]benzimidazol-1(2H)-one. The reaction mixture was heated in 60° C. for 24 hrs. The excess morpholine was removed by rotary evaporation and finally by high vacuum (0.5 mm Hg ~60° C.). The residue was dissolved in ~100 mL of CH2Cl2 washed with 3×50 ml of 1N NaOH, dried over Na2SO4, filtered, and concentrated by rotary evaporation. The residue was crystallized from isopropyl ether to give 2.7 g (65%) of analytically pure crystals, mp 111°-12° C.

Workup

  1. customThe excess morpholine was removed by rotary evaporation and finally by high vacuum (0.5 mm Hg ~60° C.)
  2. dissolutionThe residue was dissolved in ~100 mL of CH2Cl2
  3. washwashed with 3×50 ml of 1N NaOH
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation
  7. customThe residue was crystallized from isopropyl ether
  8. customto give 2.7 g (65%) of analytically pure crystals, mp 111°-12° C.

Sources & evidence

ORD record
ord-7703edcb36b048dc9afb2e9593ef9a78
Source dataset
uspto-grants-1991_11
Patent number
US05063228

Linked notes

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