4-Phenylpiperidine → HCID 67041967, compound

HRID 1405492Notes

Reaction equation

Cl[C:2]1[C:11](Cl)=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:8]=2)[N:3]=1.[C:18]1([CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CC[N:32]([CH:36]([CH3:38])C)[CH:33]([CH3:35])C>CN(C)C=O>[C:18]1([CH:24]2[CH2:25][CH2:26][N:27]([C:2]3[C:11]([N:32]4[CH2:33][CH2:35][CH:13]([C:7]5[CH:8]=[CH:9][CH:4]=[CH:5][CH:6]=5)[CH2:38][CH2:36]4)=[N:10][C:9]4[C:4](=[CH:5][CH:6]=[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:8]=4)[N:3]=3)[CH2:28][CH2:29]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Into a 20-mL sealed tube, was placed a solution of ethyl 2,3-dichloroquinoxaline-6-carboxylate (150 mg, 0.55 mmol, 1.00 equiv), 4-phenylpiperidine (298 mg, 1.85 mmol, 3.00 equiv), DIEA (398 mg, 3.09 mmol, 5.00 equiv) in N,N-dimethylformamide (10 mL). The resulting solution was stirred overnight at 100° C. in an oil bath. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10). This resulted in 180 mg (62%) of ethyl 2,3-bis(4-phenylpiperidin-1-yl)quinoxaline-6-carboxylate as a yellow solid.

Workup

customInto a 20-mL sealed tube
concentrationThe resulting mixture was concentrated under vacuum
customThis resulted in 180 mg (62%) of ethyl 2,3-bis(4-phenylpiperidin-1-yl)quinoxaline-6-carboxylate as a yellow solid

Sources & evidence

ORD record: ord-01186c4678ac489db2bad6509b294ea2
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916560B2

Reaction notes

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