Triethylamine → HCID 21919657, compound

HRID 491555Notes

Reaction equation

HRID 491555 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-eec72ceae00e4fa495da5c8241497834
Source dataset
uspto-grants-2009_05
Patent number
US07531549B2

Reaction notes

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