Triethylamine → HCID 30288965, compound

HRID 559321Notes

Reaction equation

HRID 559321 reaction equation
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=1)[CH:11]=[CH:12][C:13]([OH:15])=O.[NH:19]1[CH2:24][CH2:23][NH:22][CH2:21][C:20]1=[O:25].C(N(CC)CC)C.S([O-])(O)(=O)=O.[K+]>ClCCl.CN(C)C=O>[Cl:7][C:8]1[CH:9]=[C:10](/[CH:11]=[CH:12]/[C:13]([N:22]2[CH2:23][CH2:24][NH:19][C:20](=[O:25])[CH2:21]2)=[O:15])[CH:16]=[CH:17][CH:18]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 746313-(3-Chlorophenyl)prop-2-enoic acidHCID 231360Piperazin-2-oneHCID 516920Potassium bisulfate

Product 1

HCID 30288965HCID 30288965, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

A solution of oxalyl chloride (4.19 g, 33.0 mmol) in dichloromethane (12.5 ml) was added dropwise at room temperature to a solution of 3-chlorocinnamic acid (5.48 g, 30.0 mmol) and N,N-dimethylformamide (2 drops) in dichloromethane (240 ml). After 2 h the solution was evaporated and the residue redissolved in dichloromethane (160 ml), then a solution of piperazin-2-one (2.70 g, 27 mmol) and triethylamine (6.07 g, 60.0 mmol) in dichloromethane (80 ml) was added dropwise at 0° C. The reaction mixture was allowed to reach room temperature over 16 h, then poured onto 10% aq. potassium hydrogensulfate solution. The organic layer was washed with sat. aq. sodium hydrogencarbonate solution and 10% aq. sodium chloride solution, dried, and evaporated to produce the title compound (5.12 g, 72%). Yellow solid, MS (EI)=264.1 (M)+.

Workup

  1. customAfter 2 h the solution was evaporated
  2. dissolutionthe residue redissolved in dichloromethane (160 ml)
  3. washThe organic layer was washed with sat. aq. sodium hydrogencarbonate solution and 10% aq. sodium chloride solution
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-eafdd0ce99ea4951b0fd89fd96615b96
Source dataset
uspto-grants-2011_11
Patent number
US08063042B2

Reaction notes

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