Triethylamine → HCID 18367365, compound

HRID 1741400Notes

Reaction equation

HRID 1741400 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. (+) APCI-MS (m/z): 278 (M+ +1) IR (Film): 1725, 1600, 1260 cm-1NMR (CDCl3, δ): 1.29 (3H, t, J=7.1 Hz), 1.50-1.85 (6H, m), 2.10-2.22 (1H, m), 2.88-3.00 (1H, m), 3.14 (1H, dd, J=6.8, 5.2 Hz), 3.40 (1H, d, J=13.4 Hz), 3.78 (1H, d, J=13.4 Hz), 3.81 (3H, s), 4.21 (2H, q, J=7.1 Hz), 6.77-6.82 (1H, m), 6.89-6.93 (2H, m), 7.17-7.27 (1H, m)

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-bd55c20eb4b4438f9bf8be2692db29e8
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

Loading…