tert-Butyl piperazine-1-carboxylate → HCID 69196157, compound

HRID 2116518Notes

Reaction equation

HRID 2116518 reaction equation
Cl[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:7]2.[N:19]1([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:13]1([O:12][C:8]2[CH:9]=[N:10][C:11]3[C:6]([CH:7]=2)=[CH:5][CH:4]=[CH:3][C:2]=3[N:22]2[CH2:21][CH2:20][N:19]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:24][CH2:23]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 23676156Sodium t-butoxideHCID 69195970HCID 69195970, compound

Product 1

HCID 69196157HCID 69196157, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

A stirred suspension of 8-chloro-3-(phenyloxy)quinoline (D7)(0.115 g, 0.45 mmol), 1,1-dimethylethyl 1-piperazinecarboxylate (0.084 g, 0.45 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.012 g, 0.014 mmol), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (0.016 g, 0.041 mmol) and sodium tert-butoxide (0.043 g, 0.45 mmol) in degassed toluene (2.5 ml) was heated in a sealed tube at 150° C. for 10 mins in a microwave oven. The cooled reaction mixture was washed with water (20 ml), dried (MgSO4) and concentrated in vacuo to an oil. The oil was purified by chromatography over silica gel eluting with a gradient of ethyl acetate/hexane to afford the title compound (D8) as a yellow oil (0.09 g, 0.22 mmol, 49%).

Workup

  1. customThe cooled reaction mixture
  2. washwas washed with water (20 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo to an oil
  5. customThe oil was purified by chromatography over silica gel eluting with a gradient of ethyl acetate/hexane

Sources & evidence

ORD record
ord-f55fe3199b7f45b4a8a9e43263d0afa2
Source dataset
uspto-grants-2008_10
Patent number
US07439243B2

Reaction notes

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