Diethyl Ether → HCID 2845510, compound

HRID 586395Notes

Reaction equation

HRID 586395 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Br)([O-:3])=[O:2].[N:12]1([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(N(CC)CC)C.C(OCC)C>CN1C(=O)CCC1>[CH2:21]([O:20][C:18]([N:12]1[CH2:13][CH2:14][N:15]([CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH2:16][CH2:17]1)=[O:19])[CH3:22]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 8471TriethylamineHCID 77568Benzene, 1-(bromomethyl)-3-nitro-

Product 1

HCID 2845510HCID 2845510, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 3-nitrobenzylbromide (2.2 g; 10.0 mmol) in NMP (5 ml) was added ethyl piperazine-1-carboxylate dropwise with stirring. At the end of the addition the temperature had reached 35° C. Triethylamine (1.39 ml) was added causing the temperature to rise to 40° C. The mixture was stirred for additionally 30 min. prior to dilution with diethyl ether (25 ml). The mixture was filtered and the filtrate was washed with water, dried over magnesium sulphate and concentrated under reduced pressure. The concentrate was suspended in diethyl ether and filtered. The filtrate was diluted with ethyl acetate and extracted with diluted hydrochloric acid. The aqueous phase was rendered alkaline by addition of saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The organic phase was dried over magnesium sulphate and evaporated to dryness to leave 6a (1.72 g; 59%).

Workup

  1. additionAt the end of the addition the temperature
  2. customhad reached 35° C
  3. customto rise to 40° C
  4. stirringThe mixture was stirred for additionally 30 min.
  5. filtrationThe mixture was filtered
  6. washthe filtrate was washed with water
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated under reduced pressure
  9. filtrationfiltered
  10. additionThe filtrate was diluted with ethyl acetate
  11. extractionextracted with diluted hydrochloric acid
  12. additionby addition of saturated aqueous sodium bicarbonate
  13. extractionextracted with ethyl acetate
  14. dry with materialThe organic phase was dried over magnesium sulphate
  15. customevaporated to dryness

Sources & evidence

ORD record
ord-c6ded55efd00488f83a8f663f96c7c94
Source dataset
uspto-grants-2005_08
Patent number
US06936613B2

Reaction notes

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