Toluene → HCID 19989848, compound

HRID 973427Notes

Reaction equation

HRID 973427 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.[F:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]([C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)C2CCNCC2)=[CH:22][CH:21]=1.C([N:42]([CH2:45][CH3:46])[CH2:43][CH3:44])C.[C:47]1(C)C=CC=CC=1>>[F:39][C:36]1[CH:37]=[CH:38][C:33]([CH:26]([CH:45]2[CH2:46][CH2:47][CH2:44][CH2:43][N:42]2[CH2:2][CH2:3][CH:4]2[C:9]3=[N:10][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[N:8]3[C:7](=[O:17])[N:6]([CH3:18])[CH2:5]2)[C:23]2[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=2)=[CH:34][CH:35]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 132505444-[Bis(4-fluorophenyl)methyl]piperidineHCID 199898454-(2-Chloroethyl)-3,4-dihydro-2-methylpyrimido[1,6-a]benzimidazol-1(2H)-one

Product 1

HCID 19989848HCID 19989848, compound

Procedure

To 4.0 g (0.015 mol) of 4-(2-chloroethyl)-3,4-dihydro-2-methylpyrimido[1,6-a]benzimidazol-1(2H)-one in 20 mL of toluene was added 5.0 g (0.0175 mol) of 4-[bis(4-fluorophenyl)methyl]piperidine and 5.0 g (0.05 mol) of triethylamine and the reaction mixture heated to reflux for 24 hr. The reaction mixture was washed with 3×50 mL of 1N NaOH, dried over Na2SO4, filtered, and concentrated by rotary evaporation. The residue was subjected to preparative HPLC using ethanol as the eluent and silica gel as the stationary phase. Like fractions were combined and concentrated by rotary evaporation to give 3.7 g (49%) of an analytically pure oil.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 24 hr
  3. washThe reaction mixture was washed with 3×50 mL of 1N NaOH
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation
  7. concentrationconcentrated by rotary evaporation
  8. customto give 3.7 g (49%) of an analytically pure oil

Sources & evidence

ORD record
ord-b8fc3ca03bda424eb9f8c51fe70e4b42
Source dataset
uspto-grants-1991_11
Patent number
US05063228

Reaction notes

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