Triethylamine → N-formyl-N'-(methacryloyloxyethyl)piperazine

HRID 974188Notes

Reaction equation

HRID 974188 reaction equation
[C:1](Cl)(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH:7]([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][OH:17])[CH2:11][CH2:10]1)=[O:8].C(N(CC)CC)C.C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>ClCCl>[CH:7]([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][O:17][C:1](=[O:5])[C:2]([CH3:4])=[CH2:3])[CH2:11][CH2:10]1)=[O:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 99422134-(2-Hydroxyethyl)piperazine-1-carbaldehyde

Product 1

HCID 14875999N-formyl-N'-(methacryloyloxyethyl)piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

105.5 g (1.01 mol) of methacryloyl chloride were added dropwise between -30° and -35° C. to a stirred solution of 160 g (1.01 mol) of N-formyl-N-'-2-hydroxyethylpiperazine, 111 g (1.10 mol) of triethylamine and 100 mg of 2,6-di-tert.-butyl-4-methylphenol in 300 ml of dichloromethane and the mixture was stirred for two hours at the same temperature. The precipitate which deposited was filtered off and the filtrate was washed with sodium chloride solution, dried and concentrated to give 166.8 g (73% of theory) of a clear oil of N-formyl-N'-(methacryloyloxyethyl)piperazine. It was possible to elute this with methanol in high purity from a silica gel column after separating small amounts of by-products with ether/n-hexane (6:4).

Workup

  1. filtrationThe precipitate which deposited was filtered off
  2. washthe filtrate was washed with sodium chloride solution
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-35a97a9f5c0f4ea881b8437c615eafc6
Source dataset
uspto-grants-1991_11
Patent number
US05068264

Reaction notes

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