Triethylamine → HCID 22395371, compound

HRID 1019260Notes

Reaction equation

HRID 1019260 reaction equation
Cl.O.[NH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.C(N(CC)CC)C.[CH2:17]([O:19][C:20]([CH2:22][CH2:23][C:24](Cl)=[O:25])=[O:21])[CH3:18]>C(Cl)Cl>[CH2:17]([O:19][C:20]([CH2:22][CH2:23][C:24]([N:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)=[O:25])=[O:21])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 84648Butanoic acid, 4-chloro-4-oxo-, ethyl esterHCID 2723901Piperonylamine

Product 1

HCID 22395371HCID 22395371, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-piperidone monohydrate hydrochloride (7.68 g, 50 mmol) and triethylamine (21 ml) in methylene chloride (100 ml) was added 3-(ethoxycarbonyl)propionyl chloride (9.87 g, 60 mmol) at 0° C. over a period of 10 min. The mixture was stirred at room temperature for 16 h before being quenched with water (100 ml). The organic layer was separated and the aqueous layer was extracted with methylene chloride (100 ml). The combined organic layers were washed with 1M HCl (100 ml), saturated aqueous sodium bicarbonate (100 ml), and brine (100 ml), dried over sodium sulfate, and concentrated. Purification by flash chromatography (silica gel, 30% ether in hexanes) gave the desired ketone (3.80 g, 33%) as a light yellow oil. 1H NMR (500 MHz, CDCl3) δ1.27 (t, J=7.3 Hz, 3H), 2.48 (t, J=6.4Hz, 2H), 2.53 (t, J=6.4 Hz, 2H), 2.68 (s, 4H), 3.82 (t, J=6.3 Hz, 2H), 3.82 (t, J=6.3 Hz, 2H), 4.16 (q, J=7.3 Hz, 2H).

Workup

  1. custombefore being quenched with water (100 ml)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with methylene chloride (100 ml)
  4. washThe combined organic layers were washed with 1M HCl (100 ml), saturated aqueous sodium bicarbonate (100 ml), and brine (100 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customPurification by flash chromatography (silica gel, 30% ether in hexanes)

Sources & evidence

ORD record
ord-9e5a40199abd473ab28caf6d925774e1
Source dataset
uspto-grants-2002_11
Patent number
US06486199B1

Reaction notes

Loading…