Ethyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochloride → Ethyl 1-benzyl-4-oxopiperidine-3-carboxylate

HRID 338765

Reaction equation

HRID 338765 reaction equation
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][C:12](=[O:15])[CH:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:2]([N:9]1[CH2:14][CH2:13][C:12](=[O:15])[CH:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:10]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 102623Ethyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 102624Ethyl 1-benzyl-4-oxopiperidine-3-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 5 L 3-necked flask equipped with a mechanical stirrer and a dropping funnel was placed ethyl 1-benzyl-4-oxo-3-piperidinecarboxylate hydrochloride, (199.3 g, 0.67 mol) in dichloromethane (1.5 L). To this suspension was added saturated sodium bicarbonate (1.5 L) over one hour. After the solid dissolved, the organic layer was separated, washed with brine (250 mL), filtered through 1 PS filter paper and concentrated under reduced pressure to give 160.5 g (92%) of ethyl 1-benzyl-4-oxo-3-piperidinecarboxylate as an oil. NMR 60 MHz, (CDCl3), δ 7.3 (s, 5H), 4.2 (q, 2H), 3.6 (s, 2H), 2.3-3.6 (m, 6H), 1.3 (t, 3H).

Workup

  1. customIn a 5 L 3-necked flask equipped with a mechanical stirrer and a dropping funnel
  2. dissolutionAfter the solid dissolved
  3. customthe organic layer was separated
  4. washwashed with brine (250 mL)
  5. filtrationfiltered through 1 PS
  6. filtrationfilter paper
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-23accd3ce0b947b5adda01e15ea94ba1
Source dataset
uspto-grants-2014_11
Patent number
US08889870B2

Linked notes

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