Isobutyl acrylate → Isobutyl 3-[4-(diphenylmethylidene)piperidin-1-yl]propanoate

HRID 2250411Notes

Reaction equation

HRID 2250411 reaction equation
[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20]([O:24][CH2:25][CH:26]([CH3:28])[CH3:27])(=[O:23])[CH:21]=[CH2:22]>C(O)C>[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:8]2[CH2:9][CH2:10][N:11]([CH2:22][CH2:21][C:20]([O:24][CH2:25][CH:26]([CH3:28])[CH3:27])=[O:23])[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 7819Isobutyl acrylateHCID 27625334-(Diphenylmethylene)piperidine

Product 1

HCID 10226922Isobutyl 3-[4-(diphenylmethylidene)piperidin-1-yl]propanoateYield 87.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 20 (0.782 g, 3.14 mmol), isobutyl acrylate (0.56 mL, 3.89 mmol) and ethanol (5 mL) was shaken at 75° C. for 2 h, then evaporated to dryness to give 1.04 g of 11e as a viscous yellow oil that was used without further purification. The structure was confirmed by 1H NMR. (Propanoate esters 11b, 11c, and 11f were similarly prepared (see synthesis of cyclopentyl acrylate in the Scheme 6).

Workup

  1. customevaporated to dryness

Sources & evidence

ORD record
ord-fecabc328ca248069d7de8ee22029570
Source dataset
uspto-grants-2008_01
Patent number
US07317026B2

Reaction notes

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