Water → Methyl 1-[(2,5-dimethylphenyl)acetyl]-4-piperidinecarboxylate

HRID 2043729Notes

Reaction equation

HRID 2043729 reaction equation
[NH:1]1[CH2:10][CH2:9][CH:4]([C:5]([O:7][CH3:8])=[O:6])[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][C:20]=1[CH2:26][C:27](Cl)=[O:28].O>ClCCl>[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][C:20]=1[CH2:26][C:27]([N:1]1[CH2:10][CH2:9][CH:4]([C:5]([O:7][CH3:8])=[O:6])[CH2:3][CH2:2]1)=[O:28]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 424914Methyl isonipecotateHCID 22561615(2,5-Dimethylphenyl)acetyl chloride

Product 1

HCID 46764330Methyl 1-[(2,5-dimethylphenyl)acetyl]-4-piperidinecarboxylateYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.86 g (20 mmol) of methyl isonipecotate and 2.53 g (2.5 mmol) of triethylamine in 10 mL of dry dichloromethane was cooled to 0° C., and a solution of 4.02 g (22 mmol) of 2,5-dimethylphenylacetyl chloride in 5 mL of dichloromethane was added dropwise. The mixture was stirred at room temperature for 16 h and then poured into 20 mL of water. The organic layer was washed with water and brine, dried (MgSO4) and concentrated under reduced pressure. The residue was crystallized from a mixture of ethyl acetate and hexanes to give 4.95 g (87.5% yield) of the title compound as white crystals.

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was crystallized from a mixture of ethyl acetate and hexanes

Sources & evidence

ORD record
ord-857ed0999fb044f78902682710867cf1
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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