Borane;tetrahydrofuran → HCID 66858189, compound

HRID 1023034Notes

Reaction equation

HRID 1023034 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=O)[CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([C:26]([F:29])([F:28])[F:27])[CH:19]=3)[CH2:14][CH2:13]2)=[C:5]([N+:31]([O-])=O)[CH:4]=1.B.O1CCCC1>O1CCCC1>[NH2:31][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[NH:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([C:26]([F:28])([F:27])[F:29])[CH:19]=2)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 66859011HCID 66859011, compound

Product 1

HCID 66858189HCID 66858189, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

N-(4-Methoxy-2-nitro-phenyl)-2-[4-(4-methoxy-3-trifluoromethyl-phenyl)-piperazin-1-yl]acetamide (6.1 g; 11 mmol) iss dissolved in 70 ml tetrahydrofurane. Borane-tetrahydrofurane complex (90 ml of 1M THF solution) is added at 10° C. and the mixture is warmed to 55° C. for 4 hours. After cooling to room temperature, the solvent is evaporated under vacuum and the residue is taken with ethanol and acidified with hydrochloric acid. Heating to 50° C. takes place for 60 min. Upon overnight cooling, the unreacted compound is separated by filtration. The liquid phase is dried under vacuum, taken up with water and, after removal of the undissolved solid, saturated sodium hydrogencarbonate solution is added. The aqueous phase is extracted with ethylacetate and the organic layer is dessicated prior to evaporation. The residue is purified by silicagel chromatography (methylene chloride/methanol/32% aqueous ammonia 95:5:0.5). The title compound can be directly used for the following step.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent is evaporated under vacuum
  3. temperatureHeating to 50° C.
  4. customfor 60 min
  5. temperatureUpon overnight cooling
  6. customthe unreacted compound is separated by filtration
  7. customThe liquid phase is dried under vacuum
  8. customafter removal of the undissolved solid, saturated sodium hydrogencarbonate solution
  9. additionis added
  10. extractionThe aqueous phase is extracted with ethylacetate
  11. customto evaporation
  12. customThe residue is purified by silicagel chromatography (methylene chloride/methanol/32% aqueous ammonia 95:5:0.5)

Sources & evidence

ORD record
ord-b51f4f6e30514461b3c859b3952d02e4
Source dataset
uspto-grants-2014_05
Patent number
US08722682B2

Reaction notes

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