Dimethylamine → HCID 10176453, compound

To a stirred solution of 6-Chloroacetyl-1-pivaloylindole (300 mg, 1.08 mmol) in THF (5 ml) were added successively, at room temperature, NaHCO3 (453.6 mg, 5.4 mmol) and a solution of 2M N,N-Dimethylamine in THF (2.7 ml, 5.4 mmol). The reaction mixture was then refluxed for four hours. After cooling to room temperature, the mixture was diluted with water (15 ml) and the organic layer extracted twice with dichloromethane (2×50 ml). After washing sequentially with water and brine, the organic layer was dried over sodium sulfate, and the solvent removed in vacuo. LiAlH4 (10.8 ml, 1M in THF, 10.8 mmol) was added to a solution of the crude product in THF (5 ml) and the reaction mixture heated at reflux overnight. After cooling to room temperature, the reaction mixture was quenched with Rochelle's salt (1 M, 3 mL) and silica gel and passed through a frit using methanolic ammonia in dichloromethane (0-10%). The 5% fraction was further purified by flash chromatography (silica gel, 3% methanolic ammonia in dichloromethane) yielding the product (176 mg, 87%) of the title product.

1. temperatureThe reaction mixture was then refluxed for four hours
2. extractionthe organic layer extracted twice with dichloromethane (2×50 ml)
3. washAfter washing sequentially with water and brine
4. dry with materialthe organic layer was dried over sodium sulfate
5. customthe solvent removed in vacuo
6. temperaturethe reaction mixture heated
7. temperatureat reflux overnight
8. temperatureAfter cooling to room temperature
9. customthe reaction mixture was quenched with Rochelle's salt (1 M, 3 mL) and silica gel
10. customThe 5% fraction was further purified by flash chromatography (silica gel, 3% methanolic ammonia in dichloromethane)

ORD record

ord-7746af2d4cd04a1db92757cd4b627939

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06716837B1