Dimethylformamide dimethyl acetal → (E)-benzyl 3-(3-(dimethylamino)acryloyl)piperidine-1-carboxylate

HRID 659604Notes

Reaction equation

HRID 659604 reaction equation
[C:1]([CH:4]1[CH2:9][CH2:8][CH2:7][N:6]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:5]1)(=[O:3])[CH3:2].[CH3:20][N:21]([CH:23](OC)OC)[CH3:22]>CN(C=O)C>[CH3:20][N:21]([CH3:23])/[CH:22]=[CH:2]/[C:1]([CH:4]1[CH2:9][CH2:8][CH2:7][N:6]([C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:11])[CH2:5]1)=[O:3]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 53249939Benzyl 3-acetylpiperidine-1-carboxylate

Product 1

HCID 70642147(E)-benzyl 3-(3-(dimethylamino)acryloyl)piperidine-1-carboxylateYield 110.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 250-mL round-bottom flask was charged with a solution of benzyl 3-acetylpiperidine-1-carboxylate (15 g, 54.53 mmol, 1.00 equiv, 95%) in DMF (100 mL). To the mixture was added DMF-DMA (17 g, 141.43 mmol, 2.50 equiv, 99%). The resulting solution was allowed to reflux for about 6 hours. The mixture was then cooled down to room temperature and concentrated on a rotary evaporator affording crude (E)-benzyl 3-(3-(dimethylamino)acryloyl)piperidine-1-carboxylate as brown oil (19 g).

Workup

  1. temperatureto reflux for about 6 hours
  2. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-1f64a01a66214cf8b72ea2db8b2b3587
Source dataset
uspto-grants-2011_12
Patent number
US08080566B1

Reaction notes

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