Triethylamine → HCID 22077710, compound

HRID 1735925Notes

Reaction equation

HRID 1735925 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8](=[O:19])/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[C:27](Cl)(=[O:31])[C:28]([CH3:30])=[CH2:29]>C(Cl)Cl>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11](/[CH:10]=[CH:9]/[C:8]([N:5]2[CH2:6][CH2:7][CH:2]([O:1][C:27](=[O:31])[C:28]([CH3:30])=[CH2:29])[CH2:3][CH2:4]2)=[O:19])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 19347577HCID 19347577, compound

Product 1

HCID 22077710HCID 22077710, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6.65 g of 4-hydroxy-(E)-1-[3-(4-methoxy-phenyl)acryloyl]-piperidine in 50 ml of methylene chloride was treated with 4 ml of triethylamine at 0° C. while gassing with argon. 2.7 ml of methacryloyl chloride were added dropwise within 15 minutes. Subsequently, the reaction mixture was concentrated to dryness in a vacuum. Chromatographic purification of the residue on silica gel with ether/hexane (vol. 4:1) gave 4.21 g of 2-methyl-acrylic acid (E)-I-[3-(4-methoxy-phenyl)-acryloyl]-piperidin-4-yl ester as a colourless oil. λmax (methylene chloride)=292.5 nm (ε=22775 l mol-1 cm-1).

Workup

  1. concentrationSubsequently, the reaction mixture was concentrated to dryness in a vacuum
  2. customChromatographic purification of the residue on silica gel with ether/hexane (vol. 4:1)

Sources & evidence

ORD record
ord-abe2c24619cd4c61bf4e22791ec10e31
Source dataset
uspto-grants-1996_07
Patent number
US05539074

Reaction notes

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