Triethylamine → HCID 21919657, compound

HRID 1244526Notes

Reaction equation

HRID 1244526 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](Cl)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH2:13]([O:15]C#C)[CH3:14].[CH2:18](N(CC)CC)[CH3:19].CCOC(C)=O>C1COCC1.CO>[C:1]([N:4]1[CH2:9][CH2:8][C:7]2([C:13](=[O:15])[CH:14]=[C:10]2[O:11][CH2:18][CH3:19])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl Acetate2×HCID 61239Ether, ethyl ethynylHCID 1009501-Acetylpiperidine-4-carbonyl chloride

Product 1

HCID 21919657HCID 21919657, compoundYield 67.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-acetyl piperidine-4-carbonyl chloride (5.0 g, 26.4 mmol) and ethoxyacetylene (4.0 g, 55.5 mmol) in THF (60 ml) was treated dropwise with triethylamine (7.6 ml, 55.0 mmol). The resulting slurry was stirred at room temperature for 5 d prior to filtration and concentration of the filtrate in vacuo. Chromatography (SiO2, 100% EtOAc to 95:5 EtOAc:MeOH) gave the title compound as a white powder (3.97 g, 17.8 mmol, 67%). δH (CDCl3, 300K) 4.79 (1H, s), 4.17 (2H, q, J 7.1 Hz), 3.87–3.81 (1H, m), 3.56–3.42 (3H, m), 2.02 (3H, s), 1.85–1.67 (4H, m), 1.39 (3H, t, J 7.1 Hz); m/z (ES+, 70V) 223.9 (MH+).

Workup

  1. filtrationto filtration and concentration of the filtrate in vacuo

Sources & evidence

ORD record
ord-e6da2f693d0e4aee9c159fe3e8b95fe6
Source dataset
uspto-grants-2006_10
Patent number
US07122556B2

Reaction notes

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