Ethanol → HCID 22330068, compound

HRID 586405Notes

Reaction equation

HRID 586405 reaction equation
F[C:2]1[CH:3]=[C:4]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[N:18]1([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C(O)C>CN1C(=O)CCC1>[CH2:27]([O:26][C:24]([N:18]1[CH2:19][CH2:20][N:21]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=2)[CH2:22][CH2:23]1)=[O:25])[CH3:28]

Participants

6

Reactant 4

HCID 702EthanolHCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 8471TriethylamineHCID 98231-Fluoro-3-nitrobenzene

Product 1

HCID 22330068HCID 22330068, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 3-fluoro-1-nitrobenzene (3.37 ml; 31.6 mmol) in NMP (5 ml) was added triethylamine (4.38 ml; 31.6 mmol) and ethyl 1-piperazinecarboxylate (4.63 ml; 31.6 mmol) and the mixture was heated to 120° C. for five days. The cooled mixture was poured into ice-water and a small volume of ethanol was added. Vigorous stirring caused the product to precipitate. The product was filtered off, washed with petroleum ether and dried to leave 6p (3.34 g; 38%).

Workup

  1. customto precipitate
  2. filtrationThe product was filtered off
  3. washwashed with petroleum ether
  4. customdried

Sources & evidence

ORD record
ord-9c6e40d37eb74bce827cd3fa5a6af5fc
Source dataset
uspto-grants-2005_08
Patent number
US06936613B2

Reaction notes

Loading…