Potassium Carbonate → 1-(4-nitro 2-(2-((tetrahydro-2H-pyran 2-yl)oxy)ethoxy)phenyl)-4-(oxetan-3-yl)piperazine

HRID 928690Notes

Reaction equation

F[C:2]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:3]=1[O:4][CH2:5][CH2:6][O:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][O:9]1.[O:21]1[CH2:24][CH:23]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH2:22]1.C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1>[N+:18]([C:15]1[CH:16]=[CH:17][C:2]([N:28]2[CH2:29][CH2:30][N:25]([CH:23]3[CH2:24][O:21][CH2:22]3)[CH2:26][CH2:27]2)=[C:3]([O:4][CH2:5][CH2:6][O:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][O:9]2)[CH:14]=1)([O-:20])=[O:19]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-(2-(2-fluoro-5- nitrophenoxy)ethoxy)tetrahydro-2H-pyran XXII (1550 mg, 5.43 mmol), 1-(oxetan-3-yl)piperazine (772 mg, 5.43 mmol) and potassium carbonate (1126.41 mg, 8.15 mmol) in NMP (6 mL) was stirred at 100° C. for 8 h. The aqueous layer was separated and extracted with EtOAc. The combined organic extracts were washed with H2O (5× to remove NMP) and brine and dried over sodium sulfate. The resulting residue was purified by column chromatography ISCO Rf (24 g column) eluting with a gradient of 100% DCM—60:35:5 DCM:Et2O:MeOH to provide 1-(4-nitro-2-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)phenyl)-4-(oxetan-3-yl)piperazine XXIII.

Workup

customThe aqueous layer was separated
extractionextracted with EtOAc
washThe combined organic extracts were washed with H2O (5× to remove NMP) and brine
dry with materialdried over sodium sulfate
customThe resulting residue was purified by column chromatography ISCO Rf (24 g column)
washeluting with a gradient of 100% DCM—60:35:5 DCM

Sources & evidence

ORD record: ord-d9ffea23c6c24743aa415afe0b13f3cf
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290505B2

Reaction notes

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