Morpholine → Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-morpholinobenzimidazole-7-carboxylate

HRID 1977382Notes

Reaction equation

HRID 1977382 reaction equation
Cl[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:20]#[N:21])=[CH:10][CH:9]=2)[C:5]2[C:22]([C:26]([O:28][CH3:29])=[O:27])=[CH:23][CH:24]=[CH:25][C:4]=2[N:3]=1.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>>[C:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:11]1[CH:12]=[CH:13][C:8]([CH2:7][N:6]2[C:5]3[C:22]([C:26]([O:28][CH3:29])=[O:27])=[CH:23][CH:24]=[CH:25][C:4]=3[N:3]=[C:2]2[N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[CH:9][CH:10]=1)#[N:21]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 15654692Methyl 2-chloro-1-[(2'-cyanobiphenyl-4-yl)methyl]benzimidazole-7-carboxylate

Product 1

HCID 15654693Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-morpholinobenzimidazole-7-carboxylateYield 77%

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 2-chloro-1-[(2′-cyanobiphenyl-4-yl)-methyl]benzimidazole-7-carboxylate (0.8 g) in morpholine (15 ml) was stirred at 100° C. for 2 hours and the reaction mixture was concentrated to dryness. The residue was extracted with ethyl acetate. The extract was washed with water, dried and evaporated. The resulting crystals were recrystallized from ethyl acetate-hexane to afford colorless prisms (0.69 g, 77%).

Workup

  1. concentrationthe reaction mixture was concentrated to dryness
  2. extractionThe residue was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. customevaporated
  6. customThe resulting crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a74e142ed1dd470e9309ed42d09bc809
Source dataset
uspto-grants-2001_05
Patent number
US06232334B1

Reaction notes

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