1-Methyl-4-(piperidin-4-yl)piperazine → HCID 71239606, compound

HRID 1403198Notes

Reaction equation

HRID 1403198 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][Si:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][CH:3]=1.[CH3:14][N:15]1[CH2:20][CH2:19][N:18]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH2:17][CH2:16]1>C1COCC1.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].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1>[CH3:14][N:15]1[CH2:20][CH2:19][N:18]([CH:21]2[CH2:26][CH2:25][N:24]([C:2]3[CH:7]=[CH:6][C:5]([C:8]#[C:9][Si:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][CH:3]=3)[CH2:23][CH2:22]2)[CH2:17][CH2:16]1

Participants

6

Reactant 2

HCID 7957071-Methyl-4-(piperidin-4-yl)piperazineHCID 4226980(4-Bromophenylethynyl)trimethylsilane

Product 1

HCID 71239606HCID 71239606, compoundYield 82.1%

Reagents, catalysts & solvents 3

HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of [(4-bromophenyl)ethynyl](trimethyl)silane (2.210 g, 8.73 mmol), Pd2(dba)3 (0.400 g, 0.436 mmol), 2-dicyclohexylphosphino-2′-(N,N′-dimethylamino)biphenyl (0.172 g, 0.436 mmol) in anhydrous THF (60 mL) was degassed and backfilled with Argon for three times. 1-Methyl-4-(piperidin-4-yl)piperazine (4.00 g, 21.82 mmol) was added and the mixture was degassed and backfilled with Argon for three times again. Finally LiHMDS 1 M in THF (17.46 mL) was added by a syringe and the mixture was heated to reflux for 2 h. After cooling to room temperature the reaction mixture was filtered on a pad of celite washing with THF (300 mL). The filtrate was evaporated under vacuum and the black oil so obtained was purified by flash chromatography on silica gel (DCM/MeOH/NH4OH 90/10/0.2) to afford the title compound as a yellow solid (2.55 g, 82%).

Workup

  1. customwas degassed
  2. customthe mixture was degassed
  3. additionFinally LiHMDS 1 M in THF (17.46 mL) was added by a syringe
  4. temperaturethe mixture was heated
  5. temperatureto reflux for 2 h
  6. filtrationwas filtered on a pad of celite
  7. washwashing with THF (300 mL)
  8. customThe filtrate was evaporated under vacuum
  9. customthe black oil so obtained
  10. customwas purified by flash chromatography on silica gel (DCM/MeOH/NH4OH 90/10/0.2)

Sources & evidence

ORD record
ord-6a57a565725b4e0a82e9644168e94c9f
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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