Pivaloyl chloride → N-(2,3-dihydro-1H-cyclopenta(b)benzofuran-7-yl)-2,2-dimethyl-propionamide

HRID 1819871Notes

Reaction equation

HRID 1819871 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.[CH3:14][C:15]([CH3:20])([CH3:19])[C:16](Cl)=[O:17]>N1C=CC=CC=1>[CH2:1]1[C:8]2[C:7]3[CH:9]=[C:10]([NH:13][C:16](=[O:17])[C:15]([CH3:20])([CH3:19])[CH3:14])[CH:11]=[CH:12][C:6]=3[O:5][C:4]=2[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 196213922,3-dihydro-1H-cyclopenta[b]benzofuran-7-ylamine

Product 1

HCID 24899952N-(2,3-dihydro-1H-cyclopenta(b)benzofuran-7-yl)-2,2-dimethyl-propionamideYield 62.2%

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 trimethylacetyl chloride (0.55 mL, 4.4 mmol) in pyridine (10 mL) provided N-(2,3-dihydro-1H-cyclopenta(b)benzofuran-7-yl)-2,2-dimethyl-propionamide (0.64 g). Mp 188.5-190.0° C.; MS m/z 258 ([M+H]+); Anal. Calcd. for C16H19NO2: C, 74.68; H, 7.44; N, 5.44; Found: C, 74.67; H, 7.43; N, 5.39.

Sources & evidence

ORD record
ord-cb95bb9133864447b77c459423d68fdf
Source dataset
uspto-grants-2009_10
Patent number
US07601856B2

Reaction notes

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