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

HRID 483482Notes

Reaction equation

HRID 483482 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

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 70865N-Phenyl-1-(phenylmethyl)-4-piperidinamineHCID 534397723-Butoxyprop-2-enoyl chloride

Product 1

HCID 54210636N-(beta-n-butoxyacryloyl)-N-(1-benzyl-4-piperidinyl)anilineYield 98%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent2×

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 to give N-(β-n-butoxyacryloyl)-N-(1-benzyl-4-piperidinyl)-aniline (2.6 g).

Workup

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

Sources & evidence

ORD record
ord-961a585b2cfe4d859a4bab81ab32d461
Source dataset
uspto-grants-1993_07
Patent number
US05225402

Reaction notes

Loading…