Isovaleryl chloride → N-(2,3-Dihydro-1 H-cyclopenta[b]benzofuran-7-yl)-3-methyl-butyramide

HRID 1819872Notes

Reaction equation

HRID 1819872 reaction equation
[CH2:1]1[C:8]2[C:7]3[CH:9]=[C:10]([NH2:13])[CH:11]=[CH:12][C:6]=3[O:5][C:4]=2[CH2:3][CH2:2]1.[C:14](Cl)(=[O:19])[CH2:15][CH:16]([CH3:18])[CH3:17]>N1C=CC=CC=1>[CH2:1]1[C:8]2[C:7]3[CH:9]=[C:10]([NH:13][C:14](=[O:19])[CH2:15][CH:16]([CH3:18])[CH3:17])[CH:11]=[CH:12][C:6]=3[O:5][C:4]=2[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 66054Isovaleryl chlorideHCID 196213922,3-dihydro-1H-cyclopenta[b]benzofuran-7-ylamine

Product 1

HCID 24899953N-(2,3-Dihydro-1 H-cyclopenta[b]benzofuran-7-yl)-3-methyl-butyramideYield 65.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Following the procedure of Example 1, 2,3-dihydro-1H-cyclopenta[b]benzofuran-7-ylamine (0.69 g, 4.0 mmol) and isovaleryl chloride (0.55 mL, 4.4 mmol) in pyridine (10 mL) provided N-(2,3-Dihydro-1 H-cyclopenta[b]benzofuran-7-yl)-3-methyl-butyramide (0.67 g). Mp 162.0-163.0° C.; Anal. Calcd. for C16H19NO2: C, 74.68; H, 7.44; N, 5.44; Found: C, 74.67; H, 7.70; N, 5.39.

Sources & evidence

ORD record
ord-03ea29ce10924dc08e05a997d3fe87b3
Source dataset
uspto-grants-2009_10
Patent number
US07601856B2

Reaction notes

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