Diisopropylamine → HCID 58097102, compound

HRID 1897937Notes

Reaction equation

HRID 1897937 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[Br:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[N:15]=1.[Cl-].[Ce+3].[Cl-].[Cl-].[CH2:25]([N:32]1[CH2:37][CH2:36][C:35](=[O:38])[CH2:34][CH2:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C.CCCCCC>[CH2:25]([N:32]1[CH2:37][CH2:36][C:35]([CH2:20][C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([Br:13])[N:15]=2)([OH:38])[CH2:34][CH2:33]1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

10

Reactant 6

HCID 7912DiisopropylamineHCID 192201-Benzyl-4-piperidoneHCID 24636Cerium(III) chlorideHCID 25517Ammonium ChlorideHCID 792052-Bromo-6-methylpyridineHCID 178418339Butyllithium

Product 1

HCID 58097102HCID 58097102, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1.11 ml of diisopropylamine in 20 ml of tetrahydrofuran was added 0.73 ml of a hexane solution containing 2.66 M n-butyl lithium at −78° C. The reaction mixture was warmed to 0° C., and then cooled to −78° C. 1.2 ml of 2-bromo-6-methylpyridine was slowly added to the reaction mixture below −70° C., followed by stirring the reaction mixture at −78° C. for 30 minutes. 1.95 g of cerium(III) chloride was added to the reaction mixture at −78° C., followed by stirring the reaction mixture at −78° C. for 1 hour. 0.98 ml of 1-benzyl-4-piperidone was slowly added to the reaction mixture below −70° C., followed by stirring the reaction mixture at −78° C. for 1 h. To the reaction mixture was added saturated aqueous ammonium chloride solution, followed by adding ethyl acetate. An insoluble matter was filtered off using Celite. The organic layer was separated, washed with water and brine, dried over anhydrous magnesium sulfate, and filtered.

Workup

  1. temperaturecooled to −78° C
  2. stirringby stirring the reaction mixture at −78° C. for 1 hour
  3. stirringby stirring the reaction mixture at −78° C. for 1 h
  4. filtrationAn insoluble matter was filtered off
  5. customThe organic layer was separated
  6. washwashed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered

Sources & evidence

ORD record
ord-f2018d6468344de1b1b1eb03d3f61fcc
Source dataset
uspto-grants-2013_08
Patent number
US08519136B2

Reaction notes

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