Water → N-(beta-n-butoxyacryloyl)-N-(1-benzyl-4-piperidinyl)aniline

HRID 266774

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:28]([O:32][CH:33]=[CH:34][C:35](Cl)=[O:36])[CH2:29][CH2:30][CH3:31].O>C(OC(C)C)(C)C>[CH2:28]([O:32][CH:33]=[CH:34][C:35]([N:14]([CH:11]1[CH2:10][CH2:9][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:13][CH2:12]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:36])[CH2:29][CH2:30][CH3:31]

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of N-(1-benzyl-4-piperidinyl)aniline (1.8 g), diisopropyl ether (20 ml) and triethylamine (0.87 g) is added dropwise a solution of β-n-butoxyacrylic acid chloride (1.4 g) in diisopropyl ether (5 ml) with stirring and heating at 70° C. After completion of dropwise addition, the mixture is further stirred with heating at the same temperature for 0.5 hour. After cooling, water is added to the reaction mixture and the mixture is subjected to extraction with ethyl acetate. The extract is washed with water and dried over magnesium sulfate. The solvent is distilled off under reduced pressure and the resulting residue is purified by silica gel column chromatography give N-(β-n-butoxyacryloyl)-N-(1-benzyl-4-piperidinyl)aniline (2.6 g).

Workup

additionAfter completion of dropwise addition
stirringthe mixture is further stirred
temperaturewith heating at the same temperature for 0.5 hour
temperatureAfter cooling
extractionthe mixture is subjected to extraction with ethyl acetate
washThe extract is washed with water
dry with materialdried over magnesium sulfate
distillationThe solvent is distilled off under reduced pressure
customthe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record: ord-76524ef1d09d412fbfaee85ea7211d6a
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05652247

Linked notes

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