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

HRID 1256022
Notes
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Reaction equation

HRID 1256022 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 7957071-Methyl-4-(piperidin-4-yl)piperazineHCID 451081931,2-Difluoro-4-methoxy-5-nitrobenzene2×

Product 1

HCID 580714331-(1-(2-Fluoro-5-methoxy-4-nitrophenyl)piperidin-4-yl)-4-methylpiperazineYield 91%

Reagents, catalysts & solvents 1

HCID 679
Dimethyl Sulfoxide
Solvent

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

  1. temperatureAfter it was cooled to RT
  2. stirringAfter the mixture was stirred at RT for 10 min
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes