Triethylamine → HCID 70239719, compound

HRID 2268024Notes

Reaction equation

HRID 2268024 reaction equation
[O:1]=[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[NH:3]1.BrCCCC[N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32].C(N(CC)CC)C>CN(C)C=O>[CH2:16]([C:31]1[CH:30]=[CH:29][CH:28]=[C:25]2[C:26]([NH:22][C:23](=[O:32])[C:24]=12)=[O:27])[CH2:4][CH2:5][CH3:13].[O:1]=[C:2]1[N:6]([CH:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[NH:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 93575N-(4-Bromobutyl)phthalimide

Product 1

HCID 70239719HCID 70239719, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

4-(2-keto-1-benzimidazolinyl)piperidine (1.04 g, 4.79 mmol), N-(4-bromobutyl)-phthalimide (1.59 g, 5.64 mmol) and triethylamine (986 mL, 7.07 mmol) were combined in 10 mL of N,N-dimethylformamide. The reaction mixture was stirred at 50° C. for 18 hours, and then concentrated in vacuo. The residue was partitioned between dichloromethane and saturated sodium bicarbonate. The phases were separated and the organic phase was dried over sodium sulfate, filtered, and evaporated to dryness in vacuo. The resulting solid was purified by “flash” chromatography (95:5:0.5 of dichloromethane:methanol:ammonium hydroxide). The product fractions were evaporated to dryness and reconcentrated twice from diethyl ether to give the title compound as a solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between dichloromethane and saturated sodium bicarbonate
  3. customThe phases were separated
  4. dry with materialthe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness in vacuo
  7. customThe resulting solid was purified by “flash” chromatography (95:5:0.5 of dichloromethane:methanol:ammonium hydroxide)
  8. customThe product fractions were evaporated to dryness

Sources & evidence

ORD record
ord-6cb40c09cf2a40c68bb47b8b4ec8e29b
Source dataset
uspto-grants-2001_12
Patent number
US06326372B1

Reaction notes

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