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

HRID 1769039Notes

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].[CH2:24]([O:26][CH2:27][CH2:28]Br)[CH3:25].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][CH2:24][O:26][CH2:27][CH3:28])[CH2:20][CH2:19]1)=[O:17])#[N:2]

Participants

Conditions

Temperature: 90 °C

Procedure

Mix 1-[(4-cyanobutyl)-1H-benzimidazol-2-yl][1-(4-piperidinyl)]methanone (4.0 g, 12.91 mmol), 2-ethoxy ethylbromide (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

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

Sources & evidence

ORD record: ord-7b61970b31ec42aebfeb36c1c6126924
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05380731

Reaction notes

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