Ammonium Chloride → HCID 22678484, compound

HRID 1837690Notes

Reaction equation

HRID 1837690 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH:16]=[C:17](Br)Br)[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1.CCCCCC.C([Li])CCC.[Cl-].[NH4+]>O1CCCC1>[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([C:16]#[CH:17])[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 226784931-[(2-Methoxy-3-piridyl)methyl]-4-(2,2-dibromovinyl)piperidineHCID 178418244HCID 178418244, compound

Product 1

HCID 22678484HCID 22678484, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

2.9 g of 1-[(2-methoxy-3-piridyl)methyl]-4-(2,2-dibromovinyl)piperidine was dissolved in 25 ml of tetrahydrofuran, and 12.3 ml of a 1.50 M n-butyllithium hexane solution was added dropwise at −78° C. After completing the dropwise addition, the mixture was further stirred at −78° C. for one hour. An aqueous saturated ammonium chloride was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and then the dried over anhydrous magnesium sulfate. The solvent was evaporated, to give the title compound as a yellow oil (quantitatively).

Workup

  1. additionthe dropwise addition
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialthe dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-7870dfc4cc154e88ba2ddb0bdef3fb80
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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