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

HRID 1769036Notes

Reaction equation

[C:1]([CH2:5][O:6][CH:7]([N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[C:18]([CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)=[O:19])[CH3:8])([O:3][CH3:4])=[O:2].Br[CH2:27][CH2:28][CH2:29][CH2:30][C:31]#[N:32].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:1]([CH2:5][O:6][CH:7]([N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[C:18]([CH:20]1[CH2:25][CH2:24][N:23]([CH2:27][CH2:28][CH2:29][CH2:30][C:31]#[N:32])[CH2:22][CH2:21]1)=[O:19])[CH3:8])([O:3][CH3:4])=[O:2]

Participants

Conditions

Temperature: 90 °C

Procedure

Mix 1-[(1-carbomethoxy methoxy ethyl)-1H-benzimidazol-2-yl][1-(4-piperidinyl)]methanone (4.45 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 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-49e232968dc240d695c771f7fa08d8da
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05380731

Reaction notes

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