Sodium Carbonate → Benzyl 4-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate

HRID 1664777Notes

Reaction equation

HRID 1664777 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9](Cl)=[O:10])=[CH:3][CH:2]=1.[NH:12]1[CH2:17][CH2:16][CH:15]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:14][CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH2:22]([O:21][C:19](=[O:20])[CH2:18][CH:15]1[CH2:16][CH2:17][N:12]([C:9]([O:8][CH2:7][C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)=[O:10])[CH2:13][CH2:14]1)[CH3:23]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 2760465Ethyl 2-(piperidin-4-yl)acetate

Product 1

HCID 12902702Benzyl 4-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylateYield 98.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl chloridocarbonate (10.5 g, 61.3 mmol) was added to a solution of ethyl piperidin-4-ylacetate (10.0 g, 58.4 mmol) and sodium carbonate (46.2 g, 438 mmol) in dichloromethane (320 mL). After 18 h, the reaction mixture was filtered and concentrated. Purification by silica gel chromatography [75% hexanes/ethyl acetate→50% hexanes/ethyl acetate)] gave the title compound (17.6 g). MS 306.1 (M+1).

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated
  3. customPurification by silica gel chromatography [75% hexanes/ethyl acetate→50% hexanes/ethyl acetate)]

Sources & evidence

ORD record
ord-be89863e21194506a79c87ed733f6e0f
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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