Dichloromethane → N,N-bis(2,2,6,6-tetramethylpiperidin-4-yl)acrylamide

HRID 453603Notes

Reaction equation

HRID 453603 reaction equation
ClCCl.[CH3:4][C:5]1([CH3:24])[CH2:10][CH:9]([NH:11][CH:12]2[CH2:17][C:16]([CH3:19])([CH3:18])[NH:15][C:14]([CH3:21])([CH3:20])[CH2:13]2)[CH2:8][C:7]([CH3:23])([CH3:22])[NH:6]1.[C:25](Cl)(=[O:28])[CH:26]=[CH2:27].[OH-].[Na+]>CN(C)C1C=CN=CC=1.O>[CH3:22][C:7]1([CH3:23])[CH2:8][CH:9]([N:11]([CH:12]2[CH2:17][C:16]([CH3:19])([CH3:18])[NH:15][C:14]([CH3:21])([CH3:20])[CH2:13]2)[C:25](=[O:28])[CH:26]=[CH2:27])[CH2:10][C:5]([CH3:24])([CH3:4])[NH:6]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 13140Acryloyl chlorideHCID 14798Sodium HydroxideHCID 5667082,2,6,6-Tetramethyl-N-(2,2,6,6-tetramethyl-4-piperidinyl)-4-piperidinamine

Product 1

HCID 22902734N,N-bis(2,2,6,6-tetramethylpiperidin-4-yl)acrylamideYield 19.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

A 2500 ml flask equipped with stirrer, termometer and dropping funnel is charged with 1000 ml of dichloromethane, 147.75 g (500 mmol) N,N-bis-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine (prepared as described in EP 838 455 A1) and 1.6 g 4-dimethylaminopyridine. Then, 47.5 g (525 mmol) of acryloylchloride are added during 4 h while keeping the temperature at 0-2° C. After additional 90 minutes of stirring the solution of 21 g (521 mmol) NaOH in 100 ml water is slowly added. The organic layer is separated, dried over MgSO4 and evaporated. The residue (174.55 g) is recrystallized 3× from acetonitrile to afford 33.78 g of the title compound as white crystals, mp 115-118° C.

Workup

  1. customA 2500 ml flask equipped with stirrer
  2. customat 0-2° C
  3. additionis slowly added
  4. customThe organic layer is separated
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe residue (174.55 g) is recrystallized 3× from acetonitrile

Sources & evidence

ORD record
ord-34ff4ad9757e42de91fc411cc24c5ada
Source dataset
uspto-grants-2013_07
Patent number
US08492511B2

Reaction notes

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