Water → Methyl 1-benzylpiperidine-4-carboxylate

HRID 2376720Notes

Reaction equation

HRID 2376720 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>C(Cl)(Cl)Cl>[CH2:18]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 424914Methyl isonipecotate

Product 1

HCID 11436222Methyl 1-benzylpiperidine-4-carboxylateYield 924.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of methyl piperidine-4-carboxylate (10.00 g, 6.4 mmol) and triethylamine (10.32 g, 10.2 mmol) in CHCl3 (100 mL), benzyl bromide (14.69 g, 8.6 mmol) was added under argon atmosphere while cooling with a water and ice bath. The mixture was stirred at room temperature overnight. CHCl3 and water were added and the two phases were separated. The aqueous phase was extracted with CHCl3. The organic phase was dried over Na2SO4 and concentrated to dryness, to afford 13.80 g of the desired compound as an orange solid (yield: 88%).

Workup

  1. customthe two phases were separated
  2. extractionThe aqueous phase was extracted with CHCl3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-c9da544a45b949b78eeb1273669ed5ba
Source dataset
uspto-grants-2008_12
Patent number
US07468376B2

Reaction notes

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