Hydrochloric Acid → HCID 66880938, compound

HRID 541957Notes

Reaction equation

HRID 541957 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]1.[ClH:24].O1CCOCC1>ClCCl>[ClH:24].[ClH:24].[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 54758744tert-Butyl 4-(2-bromo-4-nitrophenyl)piperazine-1-carboxylate

Product 1

HCID 66880938HCID 66880938, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of tert-butyl 4-(2-bromo-4-nitrophenyl)piperazine-1-carboxylate (2.3 g, 5.9 mmol) in dichloromethane (15 mL) was treated with 4 M HCl in 1,4-dioxane (15 mL, 59 mmol) and stirred at 20° C. for 3 h. The reaction mixture was concentrated, diluted with a minimal amount of methanol (˜15 mL), and added dropwise to ether (300 mL) that was cooled 0° C. The solid that precipitated was collected by filtration and dried to give the desired product (1.9 g, 89%) which was used in the next step without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with a minimal amount of methanol (˜15 mL)
  3. additionadded dropwise to ether (300 mL) that
  4. temperaturewas cooled 0° C
  5. customThe solid that precipitated
  6. filtrationwas collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-5dce2352ed5a4c0da81790d42efa643b
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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