Triethylamine → HCID 21919657, compound

HRID 507708Notes

Reaction equation

HRID 507708 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%). 5H (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-de88df1c7e9440fea3ea055ad54272f7
Source dataset
uspto-grants-2010_08
Patent number
US07786177B2

Reaction notes

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