tert-Butyl piperazine-1-carboxylate → HCID 69197380, compound

HRID 2116515Notes

Reaction equation

HRID 2116515 reaction equation
Cl[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=1)=[CH:7]2.[N:20]1([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.CC(C)([O-])C.[Na+]>O1CCOCC1.ClCCl.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]>[Cl:19][C:15]1[CH:14]=[C:13]([CH2:12][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:23]2[CH2:22][CH2:21][N:20]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:25][CH2:24]2)[CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 23676156Sodium t-butoxideHCID 69195672HCID 69195672, compound

Product 1

HCID 69197380HCID 69197380, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A stirred suspension of 8-chloro-3-[(3-chlorophenyl)methyl]quinoline (D3)(0.25 g, 0.87 mmol), 1,1-dimethylethyl 1-piperazinecarboxylate (0.228 g, 1.2 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.025 g, 0.027 mmol), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (0.03 g, 0.076 mmol) and sodium tert-butoxide (0.118 g, 1.23 mmol) in degassed 1,4-dioxan (3.8 ml) under argon was heated at 80° C. under argon of 18 h. The cooled reaction mixture was diluted with dichloromethane (50 ml) and washed with water (50 ml), dried (MgSO4) and concentrated in vacuo to an oil. The oil was purified by chromatography over silica gel eluting with a gradient of acetone/toluene to give the title compound (D4) as an oil (0.202 g, 0.46 mmol, 53%).

Workup

  1. customThe cooled reaction mixture
  2. washwashed with water (50 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 acetone/toluene

Sources & evidence

ORD record
ord-1588168f77754a039d6231bb27ecdc7f
Source dataset
uspto-grants-2008_10
Patent number
US07439243B2

Reaction notes

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