Sodium Hydroxide → HCID 67492670, compound

HRID 1922382Notes

Reaction equation

Br[CH:2]([CH3:19])[C:3]([N:5]([CH:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[Al+3].[Cl-].[Cl-].[Cl-].[OH-].[Na+]>O>[CH3:19][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)[C:3]1=[O:4]

Participants

Conditions

Temperature: 185 °C

Procedure

2-Bromo-N-(1-methylpiperidin-4-yl)-N-phenylpropanamide (0.31 g, 0.953 mmol) was treated with anhydrous AlCl3 (0.5 g) and the resulting mixture was stirred at 185° C. for 2.5 h. The reaction was brought to room temperature, diluted with water (20 mL), then basified with 1 N NaOH solution (25 mL) and product was extracted into ethyl acetate (2×20 mL). The combined ethyl acetate layer was washed with brine (15 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (MeOH:CH2Cl2, 5:95) to obtain 3-methyl-1-(1-methylpiperidin-4-yl)indolin-2-one (0.19 g, 82%) a solid. 1H NMR (DMSO-d6) δ: 1.31 (d, 3H, J=7.5 Hz), 1.50-1.58 (m, 2H), 1.99 (t, 2H, J=11.7 Hz), 2.20 (s, 3H), 2.32-2.42 (m, 2H), 2.84-2.90 (m, 2H), 3.44 (q, 1H), 3.99-4.10 (m, 1H), 7.00 (t, 1H, J=7.2 Hz), 7.12 (d, 1H, J=7.8 Hz), 7.23 (t, 1H, J=7.8 Hz), 7.30 (d, 1H, J=7.5 Hz); ESI-MS (m/z, %) 245 (MH+, 100).

Workup

customwas brought to room temperature
extractionwas extracted into ethyl acetate (2×20 mL)
washThe combined ethyl acetate layer was washed with brine (15 mL)
dry with materialdried (Na2SO4)
customSolvent was evaporated
customcrude was purified by column chromatography (MeOH:CH2Cl2, 5:95)

Sources & evidence

ORD record: ord-2836d6f29aea43438701e0df46a0a32a
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173813B2

Reaction notes

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