Bromide ion → Benzyl 4-methylidenepiperidine-1-carboxylate

HRID 2300143Notes

Reaction equation

HRID 2300143 reaction equation
[Br-].[C:2](O[K])([CH3:5])([CH3:4])[CH3:3].O=C1C[CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:11]C1>O1CCCC1>[CH2:3]=[C:2]1[CH2:5][CH2:11][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:13][CH2:4]1

Participants

5

Reactant 3

HCID 259Bromide ionHCID 643496Benzyl 4-oxopiperidine-1-carboxylateHCID 178418922HCID 178418922, compound

Product 1

HCID 15519136Benzyl 4-methylidenepiperidine-1-carboxylateYield 159.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

51.1 g of methyltoluphenylphosphonium bromide was added to a mixture of 16.1 g tert-butoxy potassium and 500 ml tetrahydrofuran, and then stirred for 1 hr and 20 min at room temperature. 16.1 g of benzyl 4-oxo-1-piperidinecarboxylate was added thereto, and the mixture was stirred for 2 hr and 40 min at room temperature. The reaction solution was evaporated, diethyl ether was added thereto, and then filtered through Celite. The filtrate was washed with water and brine, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was evaporated, and the resulting residue was subjected to silica gel column chromatography to give 25.5 g of benzyl 4-methylene-1-piperidinecarboxylate.

Workup

  1. stirringthe mixture was stirred for 2 hr and 40 min at room temperature
  2. customThe reaction solution was evaporated
  3. additiondiethyl ether was added
  4. filtrationfiltered through Celite
  5. washThe filtrate was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-38d2746c90ab49d69f41b89142ceb2ac
Source dataset
uspto-grants-2002_12
Patent number
US06498159B1

Reaction notes

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