Sodium Carbonate → 1-Benzyl 4-ethyl piperidine-1,4-dicarboxylate

HRID 746995Notes

Reaction equation

HRID 746995 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH:12]1[CH2:22][CH2:21][CH:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14][CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH2:19]([O:18][C:16]([CH:15]1[CH2:21][CH2:22][N:12]([C:2]([O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:3])[CH2:13][CH2:14]1)=[O:17])[CH3:20]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 152896721-Benzyl 4-ethyl piperidine-1,4-dicarboxylateYield 94.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of benzyl chloroformate (95 g, 0.56 mol) in dichloromethane (200 ml) was added dropwise to an ice-bath-cooled, stirred mixture of ethyl isonipecotate (87 g, 0.55 mol), sodium carbonate (60 g, 0.57 mol) and dichloromethane (200 ml) over 70 minutes. The mixture was stirred at ambient temperature for 2.5 days and filtered though a pad of Celite™. The filtrate was concentrated in vacuo. The residue was partitioned between 2M aqueous hydrochloric acid and diethyl ether. Organic layer was separated, dried (MgSO4), filtered and concentrated. The residue was chromatographed on silica gel (ethyl acetate/iso-hexane) to give the title product (152 g, 94%).

Workup

  1. temperaturebath-cooled
  2. stirringThe mixture was stirred at ambient temperature for 2.5 days
  3. filtrationfiltered though a pad of Celite™
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe residue was partitioned between 2M aqueous hydrochloric acid and diethyl ether
  6. customOrganic layer was separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was chromatographed on silica gel (ethyl acetate/iso-hexane)

Sources & evidence

ORD record
ord-2adb3cd44dbb451187382347458cab56
Source dataset
uspto-grants-2008_07
Patent number
US07393858B2

Reaction notes

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