Water → N-methyl-N-(3-methyl-1H-inden-2-ylmethyl)acrylamide

HRID 1761118Notes

Reaction equation

Cl.[CH3:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C:4]=1[CH2:12][NH:13][CH3:14].C(N(CC)CC)C.[C:22](Cl)(=[O:25])[CH:23]=[CH2:24].O>C(Cl)Cl>[CH3:14][N:13]([CH2:12][C:4]1[CH2:5][C:6]2[C:11]([C:3]=1[CH3:2])=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:22](=[O:25])[CH:23]=[CH2:24]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-methyl-2-(methylaminomethyl)indene hydrochloride (0.132 g, 0.63 mmole), from Preparation 19, and triethylamine (0.19 g, 1.89 mmole) in CH2Cl2 (6 mL) at 0° C. was added a solution of acryloyl chloride (0.06 mL, 0.7 mmole) in CH2Cl2 (2 mL). The reaction was stirred at 0° C. for 1 hr. then was poured into water. The layers were separated, and the organic layer was washed with brine, dried over Mg SO4 and concentrated in vacuo to yield the title compound (0.145 g. quantitative) as an oily solid: MS (ES) m/e 228.2 (M+H)+.

Workup

customThe layers were separated
washthe organic layer was washed with brine
dry with materialdried over Mg SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f678d2204a36409a93532f66f26b2073
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06846819B1

Reaction notes

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