HCID 59403001, compound → 3-{[7-(3-Thienyl)heptyl]oxy}benzenecarboxamide

HRID 538497Notes

Reaction equation

HRID 538497 reaction equation
[S:1]1[CH:5]=[CH:4][C:3](/[CH:6]=[CH:7]\[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:15]=[C:16]([C:20]([NH2:22])=[O:21])[CH:17]=[CH:18][CH:19]=2)=[CH:2]1>CO.[Pd]>[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:15]=[C:16]([C:20]([NH2:22])=[O:21])[CH:17]=[CH:18][CH:19]=2)=[CH:2]1

Participants

4

Reactant 1

HCID 59403001HCID 59403001, compound2×

Product 1

HCID 594028973-{[7-(3-Thienyl)heptyl]oxy}benzenecarboxamideYield 48%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of example 62 3-{[(Z)-7-(3-Thienyl)-6-heptenyl]oxy}benzene carboxamide (260 mg, 0.82 mmol) in MeOH (8 ml), 10% Pd/C (30 mg) was added. The mixture was stirred under H2 at r.t for 3 days. The catalyst was removed by filtration through a pad of Celite and the solvent was evaporated under reduced pressure, to a small volume. The precipitant solid was filtered and rinsed with Et2O/pentane to give the desired compound as a white solid (130 mg, 48%), mp 97-100° C. HPLC-MS (method 1): m/z 318 [M+H]+, Rt=4.87 min.

Workup

  1. customThe catalyst was removed by filtration through a pad of Celite
  2. customthe solvent was evaporated under reduced pressure, to a small volume
  3. filtrationThe precipitant solid was filtered
  4. washrinsed with Et2O/pentane

Sources & evidence

ORD record
ord-a0e6086facd946b3a54957f8fa0cdecd
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

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