Sodium Bicarbonate → 1-(1-(2-Fluoro-5-methoxy-4-nitrophenyl)piperidin-4-yl)-4-methylpiperazine

HRID 1256022Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

1,2-Difluoro-4-methoxy-5-nitrobenzene (INTERMEDIATE 52) (1.0 g, 5.3 mmol) and 1-methyl-4-(piperidin-4-yl)piperazine (1.066 g, 5.8 mmol) were added in a 50 mL round-bottomed flask. DMSO (6 mL) was added. The reaction was stirred at 90° C. for 1 h. After it was cooled to RT, sat. NaHCO3 (20 mL) was added. After the mixture was stirred at RT for 10 min, filtration afforded the title product as an orange solid (1.7 g, 90% yield).

Workup

temperatureAfter it was cooled to RT
stirringAfter the mixture was stirred at RT for 10 min
filtrationfiltration

Sources & evidence

ORD record: ord-2fd1719e7bee4196aea3fcd861264721
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461170B2

Reaction notes

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