Potassium Carbonate → N-(4-chlorophenethyl)-4-(2-cyclopropyl-4-formylphenoxy)benzamide

HRID 453529Notes

Reaction equation

[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH:26]1([C:29]2[CH:30]=[C:31]([CH:34]=[CH:35][C:36]=2F)[CH:32]=[O:33])[CH2:28][CH2:27]1>CS(C)=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][C:13]([O:16][C:36]3[CH:35]=[CH:34][C:31]([CH:32]=[O:33])=[CH:30][C:29]=3[CH:26]3[CH2:27][CH2:28]3)=[CH:12][CH:11]=2)=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 85 °C

Procedure

N-(4-Chlorophenethyl)-4-hydroxybenzamide (504 mg, 1.83 mmol) was diluted with DMSO (8 mL) and K2CO3 (379 mg, 2.74 mmol) and 3-cyclopropyl-4-fluorobenzaldehyde (300 mg, 1.83 mmol) were added. The reaction was stirred 85° C. overnight. The reaction was cooled to ambient temperature, diluted with ethyl acetate and washed with twice with 10% sodium carbonate, water and brine, and concentrated. The crude material was purified by silica gel chromatography eluting with hexanes:ethyl acetate (3:1) to provide N-(4-chlorophenethyl)-4-(2-cyclopropyl-4-formylphenoxy)benzamide (160 mg, 20.9% yield).

Workup

additionwere added
temperatureThe reaction was cooled to ambient temperature
washwashed with twice with 10% sodium carbonate, water and brine
concentrationconcentrated
customThe crude material was purified by silica gel chromatography
washeluting with hexanes:ethyl acetate (3:1)

Sources & evidence

ORD record: ord-2b036354a8e24d1a8a6bb50aaf31a71b
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492437B2

Reaction notes

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