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

HRID 2112706Notes

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-2d33e4e8fa0c490ab0d11df63df4b9d3
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07524843B2

Reaction notes

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