Sodium Carbonate → HCID 67493865, compound

HRID 408638Notes

Reaction equation

HRID 408638 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[Na+].Cl[C:21]1[N:26]=[CH:25][C:24]([C:27]23[CH2:33][N:30]([CH2:31][CH2:32]2)[CH2:29][CH2:28]3)=[CH:23][CH:22]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:21]2[N:26]=[CH:25][C:24]([C:27]34[CH2:33][N:30]([CH2:29][CH2:28]3)[CH2:31][CH2:32]4)=[CH:23][CH:22]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 10340Sodium CarbonateHCID 759941-BenzylpiperazineHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 23676156Sodium t-butoxideHCID 59187099HCID 59187099, compound

Product 1

HCID 67493865HCID 67493865, compoundYield 39.6%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

0.055 g (0.32 mmol) of 1-benzylpiperazine is introduced into a 50 ml round-bottomed flask under argon comprising 0.036 g (0.37 mmol) of sodium tert-butoxide in solution in 5 ml of toluene through which argon has been bubbled beforehand. 0.06 g (0.29 mmol) of 4-(6-chloropyridin-3-yl)-1-azabicyclo[2.2.1]heptane obtained in stage 5.1 of Example 5, 0.003 g (0.01 mmol) of palladium(II) acetate and 0.011 g (0.03 mmol) of 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl are then successively added under an argon atmosphere. The mixture is heated at 100° C. for 3 hours, cooled to ambient temperature, diluted with 40 ml of dichloromethane and poured into 300 ml of a saturated aqueous sodium carbonate solution. The aqueous phase is extracted twice with 100 ml of dichloromethane, and the combined organic phases are dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by chromatography on a column of silica gel, elution being carried out with a mixture of chloroform, methanol and aqueous ammonia in the proportions 90/10/1. 0.04 g of the expected product is obtained in the form of a beige powder.

Workup

  1. customhas been bubbled beforehand
  2. temperaturecooled to ambient temperature
  3. extractionThe aqueous phase is extracted twice with 100 ml of dichloromethane
  4. dry with materialthe combined organic phases are dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by chromatography on a column of silica gel, elution
  7. additionbeing carried out with a mixture of chloroform, methanol and aqueous ammonia in the proportions 90/10/1

Sources & evidence

ORD record
ord-71988e17ff6449eb9b0dbaea7e5c07a6
Source dataset
uspto-grants-2014_06
Patent number
US08759343B2

Reaction notes

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