Dimethylformamide → 1-[(4-Cyanobutyl)-1H-benzimidazol-2-yl][1-(4-cyanobutyl)-4-piperidinyl]methanone

HRID 1769040Notes

Reaction equation

HRID 1769040 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[C:16]([CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)=[O:17])#[N:2].Br[CH2:25][CH2:26][CH2:27][CH2:28][C:29]#[N:30].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[C:16]([CH:18]1[CH2:23][CH2:22][N:21]([CH2:25][CH2:26][CH2:27][CH2:28][C:29]#[N:30])[CH2:20][CH2:19]1)=[O:17])#[N:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 794355-BromopentanenitrileHCID 189465181-[(4-cyanobutyl)-1H-benzimidazol-2-yl][1-(4-piperidinyl)]methanone

Product 1

HCID 189465151-[(4-Cyanobutyl)-1H-benzimidazol-2-yl][1-(4-cyanobutyl)-4-piperidinyl]methanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Mix 1-[(4-cyanobutyl)-1H-benzimidazol-2-yl][1-(4-piperidinyl)]methanone (4.0 g, 12.91 mmol), 5-bromovaleronitrile (2.5 g, 15.3 mmol), potassium carbonate (5.29 g, 38.25 mmol) and dimethylformamide (100 mL). Stir and heat at 90° C. overnight. Allow to cool to room temperature, dilute with water and extract with ethyl acetate (2×). Wash the combined organic phases with water (3×), then brine and dry (MgSO4). Evaporate the solvent in vacuo and purify by chromatography to give the title compound.

Workup

  1. temperatureto cool to room temperature
  2. extractionextract with ethyl acetate (2×)
  3. washWash the combined organic phases with water (3×)
  4. dry with materialbrine and dry (MgSO4)
  5. customEvaporate the solvent in vacuo
  6. custompurify by chromatography

Sources & evidence

ORD record
ord-34d4d0fe5e6b4b46bf5834e7d6a7afb2
Source dataset
uspto-grants-1995_01
Patent number
US05380731

Reaction notes

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