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

HRID 225923Notes

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 MgSO4 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 MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-733b063024de43638a9e5b2e43108cc3
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557125B2

Reaction notes

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