2,4,6-Trimethylbenzeneacetyl chloride → HCID 68299237, compound

HRID 1844667Notes

Reaction equation

HRID 1844667 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH:4]([OH:14])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([O:12][CH3:13])[CH2:8][CH2:7]1.[CH3:16][C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[C:18]=1[CH2:25][C:26](Cl)=[O:27]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:15])[CH:4]([O:14][C:26](=[O:27])[CH2:25][C:18]1[C:17]([CH3:16])=[CH:22][C:21]([CH3:23])=[CH:20][C:19]=1[CH3:24])[CH2:5][CH:6]1[CH2:7][CH2:8][N:9]([O:12][CH3:13])[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 110307542,4,6-Trimethylbenzeneacetyl chlorideHCID 68299236HCID 68299236, compound

Product 1

HCID 68299237HCID 68299237, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-hydroxy-3-(1-methoxy-piperidin-4-yl)-propionic acid methyl ester (700 mg, 3.5 mmol) and (2,4,6-trimethyl-phenyl)-acetyl chloride (700 mg, 3.6 mmol) in 10 ml of toluene was refluxed for 6 h. Then, the reaction mixture was concentrated under vacuum to dryness and the residue was purified by column chromatography on silica gel. Yield: 520 mg of 3-(1-methoxy-piperidin-4-yl)-2-[2-(2,4,6-trimethyl-phenyl)-acetoxy]-propionic acid methyl ester (title compound P3.12) as a oil.

Workup

  1. temperaturewas refluxed for 6 h
  2. concentrationThen, the reaction mixture was concentrated under vacuum to dryness
  3. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b55de05741564bebb5231697d31d4883
Source dataset
uspto-grants-2015_02
Patent number
US08946453B2

Reaction notes

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