Tris(1,1-dimethylethyl)phosphine → 1-[4-(4-Amino-3-methyl-5-nitro-phenyl)-piperazin-1-yl]-ethanone

HRID 1354613Notes

Reaction equation

HRID 1354613 reaction equation
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([NH2:11])=[C:4]([CH3:12])[CH:3]=1.[C:13]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)(=[O:15])[CH3:14].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:11][C:5]1[C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]([N:19]2[CH2:20][CH2:21][N:16]([C:13](=[O:15])[CH3:14])[CH2:17][CH2:18]2)=[CH:3][C:4]=1[CH3:12]

Participants

7

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 837951-AcetylpiperazineHCID 5226794-Bromo-2-methyl-6-nitroanilineHCID 23676156Sodium t-butoxide

Product 1

HCID 220210541-[4-(4-Amino-3-methyl-5-nitro-phenyl)-piperazin-1-yl]-ethanone

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 4-bromo-2-methyl-6-nitro-phenylamine (5 g, 21.64 mmol), 1-acetylpiperazine (4.2 g, 32.46 mmol), palladium acetate (244 mg, 1.08 mmol), tri-tert-butylphosphine (440 mg, 2.16 mmol) and sodium tert-butoxide (4.2 g, 43.29 mmol) in toluene (70 mL) was heated to

Workup

  1. temperaturewas heated to

Sources & evidence

ORD record
ord-d0286ff1feee47eaaf2c67cbf4064161
Source dataset
uspto-grants-2007_05
Patent number
US07223757B2

Reaction notes

Loading…