Triethylamine → HCID 21919657, compound

HRID 1783740Notes

Reaction equation

HRID 1783740 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-a1f1cf96a691447386249bc1a58d5c3a
Source dataset
uspto-grants-2009_03
Patent number
US07501437B2

Reaction notes

Loading…