Potassium Carbonate → 6-(2-(4-p-tolylpiperidin-1-yl)ethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 1184438Notes

Reaction equation

Cl[CH2:2][CH2:3][C:4]1[CH:14]=[CH:13][C:7]2[O:8][CH2:9][C:10](=[O:12])[NH:11][C:6]=2[CH:5]=1.[C:15]1([CH3:27])[CH:20]=[CH:19][C:18]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:15]1([CH3:27])[CH:16]=[CH:17][C:18]([CH:21]2[CH2:22][CH2:23][N:24]([CH2:2][CH2:3][C:4]3[CH:14]=[CH:13][C:7]4[O:8][CH2:9][C:10](=[O:12])[NH:11][C:6]=4[CH:5]=3)[CH2:25][CH2:26]2)=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a 20 mL screw cap vial was added 123 (100 mg, 0.472 mmol), 4-p-tolylpiperidine (83 mg, 0.472 mmol), K2CO3 (131 mg, 0.945 mmol) in DMF (2 mL). The reaction was stirred at 80° C. for 4 h. The reaction was filtered and the crude material was purified by prep HPLC-MS using a 25-95% MeCN in water gradient. The appropriate fractions were collected and concentrated in vacuo to give the title compound as a white solid: 1H NMR (DMSO-d6, 400 MHz): δ=10.79 (br. s., 1H), 9.27 (br. s., 1H), 7.14 (br. s., 4H), 6.94 (br. s., 1H), 6.80-6.87 (m, 1H), 6.78 (br. s., 1H), 4.56 (br. s., 2H), 3.65 (br. s., 2H), 3.27 (br. s., 2H), 3.08 (br. s., 2H), 2.94 (br. s., 2H), 2.78 (br. s., 1H), 2.28 (br. s., 3H), 2.00 (br. s., 2H), 1.82 ppm (br. s., 2H). ESI-MS: m/z 351.2 (M+H)+.

Workup

customTo a 20 mL screw cap
filtrationThe reaction was filtered
customthe crude material was purified by prep HPLC-MS
customThe appropriate fractions were collected
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-3d6dda5517ab41309fc71d1464590c61
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669249B2

Reaction notes

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