3,3-Dimethylbutanoyl chloride → N-(2,3-dihydro-1 H-cyclopenta[b]benzofuran-7-yl)-3,3-dimethyl-butyramide

HRID 1819870Notes

Reaction equation

HRID 1819870 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]([CH2:18][C:19](Cl)=[O:20])([CH3:17])([CH3:16])[CH3:15]>N1C=CC=CC=1>[CH2:1]1[C:8]2[C:7]3[CH:9]=[C:10]([NH:13][C:19](=[O:20])[CH2:18][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:11]=[CH:12][C:6]=3[O:5][C:4]=2[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 815143,3-Dimethylbutanoyl chlorideHCID 196213922,3-dihydro-1H-cyclopenta[b]benzofuran-7-ylamine

Product 1

HCID 24899951N-(2,3-dihydro-1 H-cyclopenta[b]benzofuran-7-yl)-3,3-dimethyl-butyramideYield 60.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Following the procedure of Example 1, 2,3-dihydro-1H-cyclopenta[b]benzofuran-7-ylamine (0.87 g, 5.0 mmol) and t-butylacetyl chloride (0.77 mL, 5.5 mmol) in pyridine (10 mL) provided N-(2,3-dihydro-1 H-cyclopenta[b]benzofuran-7-yl)-3,3-dimethyl-butyramide (0.82 g). Mp 195.5-197.0 ° c; MS (El) m/z 272 ([M+H]+); Anal. Calcd. for C17H21NO2: C, 75.25; H, 7.80; N, 5.16; Found: C, 75.34; H, 7.82; N, 5.14.

Sources & evidence

ORD record
ord-d4dd244b48634f42bbb75fba783ef98d
Source dataset
uspto-grants-2009_10
Patent number
US07601856B2

Reaction notes

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