Triethylamine → HCID 18367365, compound

HRID 380134Notes

Reaction equation

HRID 380134 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17]Cl.C(N(CC)CC)C>CN(C)C=O>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17][N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27517Ethyl piperidine-2-carboxylateHCID 699943-Methoxybenzyl chloride

Product 1

HCID 18367365HCID 18367365, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 2-piperidinecarboxylate (10.0 ml), 3-methoxybenzyl chloride (9.2 ml), and triethylamine (26.6 ml) in N,N-dimethylformamide (64.0 ml) was stirred at room temperature overnight and partitioned between ethyl acetate and water. The organic layer was separated, washed with water (four times) and brine, dried over MgSO4, and evaporated in vacuo. The residue was chromatographed over silica gel to afford ethyl 1-(3-methoxybenzyl)-2-piperidinecarboxylate (12.06 g) as a colorless oil.

Workup

  1. custompartitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with water (four times) and brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-ff299a2e2603483897310e35f6b34a53
Source dataset
uspto-grants-2001_10
Patent number
US06300344B1

Reaction notes

Loading…