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

HRID 1921053Notes

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-ad4c0e5563e14111bf30a567ba3f4334
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173646B2

Reaction notes

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