Benzyl acrylate → Benzyl 3-(4-acetamidopiperidin-1-yl)propanoate

HRID 889179Notes

Reaction equation

HRID 889179 reaction equation
[C:1]([NH:4][CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)(=[O:3])[CH3:2].[C:11]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:14])[CH:12]=[CH2:13]>C(#N)C>[C:1]([NH:4][CH:5]1[CH2:10][CH2:9][N:8]([CH2:13][CH2:12][C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 75617Benzyl acrylateHCID 14451564-Acetamidopiperidine

Product 1

HCID 66760069Benzyl 3-(4-acetamidopiperidin-1-yl)propanoateYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

A stirred mixture of 4-acetamidopiperidine (1.82 g, 12.8 mmol) and benzyl acrylate (2.57 g, 15.4 mmol) in acetonitrile (50 mL) was stirred overnight under nitrogen and at 40° C. for 1 h. The mixture was evaporated to dryness and the residue was purified by silica gel chromatograph eluting with a gradient of 0% to 30% dichloromethane/methanol/NH4OH (10:1:0.1) and dichloromethane to give benzyl 3-(4-acetamidopiperidin-1-yl)propanoate as an oil (3.81 g, 98%).

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe residue was purified by silica gel chromatograph
  3. washeluting with a gradient of 0% to 30% dichloromethane/methanol/NH4OH (10:1:0.1) and dichloromethane

Sources & evidence

ORD record
ord-b9414ba86b164639a45c417e61633712
Source dataset
uspto-grants-2012_08
Patent number
US08252793B2

Reaction notes

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