Dimethylformamide → HCID 57294109, compound

HRID 1769032Notes

Reaction equation

HRID 1769032 reaction equation
[CH3:1][CH2:2][O:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[C:15]([CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:16].[C:23]([CH2:27][O:28][CH2:29][CH2:30]Br)([O:25][CH3:26])=[O:24].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:1][CH2:2][O:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[C:15]([CH:17]1[CH2:18][CH2:19][N:20]([CH2:30][CH2:29][O:28][CH2:27][C:23]([O:25][CH3:26])=[O:24])[CH2:21][CH2:22]1)=[O:16]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 15228076HCID 15228076, compoundHCID 18946503Methyl (2-bromoethoxy)acetate

Product 1

HCID 57294109HCID 57294109, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Mix 1-[[(2-ethoxy)ethyl]-1H-benzimidazol-2-yl][1-(4-piperidinyl)]methanone (3.89 g, 12.91 mmol), carbomethoxy methoxy ethylbromide (3.01 g, 15.3 mmol), potassium carbonate (5.29 g, 38.25 mmol) and dimethylformamide (100 mL). Stir and heat and 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 to give 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. customto give
  7. custompurify by chromatography

Sources & evidence

ORD record
ord-db487e8cddab40ceaad5bdbe49b36991
Source dataset
uspto-grants-1995_01
Patent number
US05380731

Reaction notes

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