Nitrogen → HCID 54447250, compound

HRID 1977904Notes

Reaction equation

HRID 1977904 reaction equation
N#N.[CH2:3]([N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[CH2:16][C:17]1[CH:22]=[CH:21][C:20](Br)=[CH:19][CH:18]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([Li])CCC.[CH3:29][C:30]1[NH:31][C:32]([CH3:41])=[CH:33][C:34]=1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=1>CCCCCC.CCOCC>[CH3:29][C:30]1[NH:31][C:32]([CH3:41])=[CH:33][C:34]=1[C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([C:20]2[CH:21]=[CH:22][C:17]([CH2:16][CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15][N:10]3[CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)=[CH:18][CH:19]=2)[N:36]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 12082743HCID 12082743, compoundHCID 53980622HCID 53980622, compoundHCID 178418339Butyllithium

Product 1

HCID 54447250HCID 54447250, compoundYield 16.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

To a 100 mL 3N round-bottomed flask equipped with septum and N2 inlet were added 175 mg (0.509 mmol) N-benzyl-2-(4-bromobenzyl)-piperidine and 7 mL dry ether. The solution was cooled to −70° C., and 0.38 mL (0.610 mmol) of a 1.6 M solution of butyl lithium in hexane added dropwise over 1 minutes. The reaction was stirred at −70° C. for 5 min, then warmed to room temperature over 20 minutes. To the stirring reaction was then added a solution of 105 mg (0.610 mmol) 2-(2,5-dimethylpyrrolyl)-pyridine in 5 mL dry ether, and the reaction, turning dark orange, was stirred at room temperature for 4 hours then quenched with aqueous ammonium chloride solution. After extraction into ethyl acetate, the organic layer was washed with brine, dried over sodium sulfate for 16 hours to effect air-oxidation to the pyridine, and evaporated. The residue was chromatographed on silica gel using methanol/methylene chloride as eluant to afford 36 mg (16%) of an oil.

Workup

  1. temperaturewarmed to room temperature over 20 minutes
  2. customTo the stirring reaction
  3. customthe reaction
  4. stirringwas stirred at room temperature for 4 hours
  5. customthen quenched with aqueous ammonium chloride solution
  6. extractionAfter extraction into ethyl acetate
  7. washthe organic layer was washed with brine
  8. dry with materialdried over sodium sulfate for 16 hours
  9. customevaporated
  10. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-fe1ab2c3fd194bc5b2a4ce7e70c7e981
Source dataset
uspto-grants-2001_05
Patent number
US06235750B1

Reaction notes

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