Dimethylformamide → 1-[[(2-Ethoxy)ethyl]-1H-benzimidazol-2-yl][1-(t-butyloxycarbonyl)-4-piperidinyl)methanone

HRID 1769030Notes

Reaction equation

HRID 1769030 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)=[O:11].[CH2:25]([O:27][CH2:28][CH2:29]Br)[CH3:26].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:26][CH2:25][O:27][CH2:28][CH2:29][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:12]1[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]1)=[O:11]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 611412-Bromoethyl ethyl etherHCID 183332351-(t-butoxycarbonyl)-4-(1H-benzimidazole-2-carbonyl)piperidine

Product 1

HCID 540144471-[[(2-Ethoxy)ethyl]-1H-benzimidazol-2-yl][1-(t-butyloxycarbonyl)-4-piperidinyl)methanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Mix [1H-benzimidazol-2-yl][1-(t-butyloxycarbonyl)-4-piperidinyl]methanone (4.25 g, 12.91 mmol), 2-bromoethyl ethyl ether (2.34 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 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-3e4334f1fbb148cabde94948c2351aba
Source dataset
uspto-grants-1995_01
Patent number
US05380731

Reaction notes

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