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Potassium Phosphate, Tribasic → 1-[(2-Cyclopropyl-4-nitrophenyl)methyl]-4-methylpiperazine

HRID 572997
Notes
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Reaction equation

HRID 572997 reaction equation
Br[C:2]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH3:11])[CH2:7][CH2:6]1.[CH:19]1(B(O)O)[CH2:21][CH2:20]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:19]1([C:2]2[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:3]=2[CH2:4][N:5]2[CH2:10][CH2:9][N:8]([CH3:11])[CH2:7][CH2:6]2)[CH2:21][CH2:20]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 468386111-[(2-Bromo-4-nitrophenyl)methyl]-4-methylpiperazine

Product 1

HCID 468386121-[(2-Cyclopropyl-4-nitrophenyl)methyl]-4-methylpiperazineYield 96.8%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 22272177Toluene waterSolvent

Procedure

A mixture of 1-(2-bromo-4-nitrobenzyl)-4-methylpiperazine (0.94 g, 3.0 mmol), 0.77 g (9.0 mmol) of cyclopropylboronic acid, 0.067 g (0.30 mmol) of Pd(OAc)2, 2.87 g (13.5 mmol) of K3PO4, and 0.168 g (0.60 mmol) of tricyclohexylphosphine in 18 mL of toluene/water (5:1) was heated at reflux under an atmosphere of N2 for 19 h. The reaction mixture was concentrated and the crude product was purified by silica gel chromatography (eluted with 5% MeOH/DCM; MeOH was pre-saturated with ammonia gas) to provide 0.80 g of product.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under an atmosphere of N2 for 19 h
  3. concentrationThe reaction mixture was concentrated
  4. customthe crude product was purified by silica gel chromatography (eluted with 5% MeOH/DCM; MeOH was pre-saturated with ammonia gas)

Sources & evidence

ORD record
ord-53134630ffeb4208aca6426caa6f0491
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09029533B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes