Hydrochloric Acid → HCID 58659410, compound

HRID 1993573Notes

Reaction equation

HRID 1993573 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:12]([N:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH3:21])[CH2:16][CH2:15]2)=O)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.B.C1COCC1.Cl.O>C1COCC1>[CH2:20]([N:17]1[CH2:18][CH2:19][N:14]([CH2:12][C:4]2[CH:3]=[C:2]([NH2:1])[CH:7]=[C:6]([C:8]([F:9])([F:11])[F:10])[CH:5]=2)[CH2:15][CH2:16]1)[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2723981Borane;tetrahydrofuranHCID 68537492HCID 68537492, compound

Product 1

HCID 58659410HCID 58659410, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3-amino-5-trifluoromethyl-phenyl)-(4-ethyl-piperazin-1-yl)-methanone (14.6 g, 48.5 mmol) in THF (120 ml) under N2-atmosphere, a 1 M solution of BH3.THF (145.5 ml) is added dropwise (exothermic). The mixture is stirred for 14 h at rt and then 5 h at 65° C. After cooling to rt, HCl conc./H2O 1:1 (250 ml) Is added and the mixture stirred for 15 h. The suspension is filtered, the filtrate extracted 3 times with AcOEt. The organic phases are washed twice with 1 N HCl and then discarded. The combined acidic phases are made basic by addition of saturated Na2CO3 solution and extracted 3 times with AcOEt. The organic layers are washed twice with water and brine, dried (Na2SO4) and concentrated. Column chromatography (SiO2; AcOEt/EtOH/NH3 95:5:1→90:10:1) followed by extraction between 3 portions of AcOEt, 3 portions of water and finally brine, drying (Na2SO4) and concentration yields the title compound as an oil: MS: [M+1]+=288; 1H-NMR (CDCl3): 6.94 (s, 1H), 6.82 (s, 1H), 6.78 (s, 1H), 3.82 (sb, H2N), 3.46 (s, 2H), 2.51 (m, 8H), 2.44 (q, 2H), 1.10 (t, 3H).

Workup

  1. custom5 h
  2. customat 65° C
  3. temperatureAfter cooling to rt
  4. stirringthe mixture stirred for 15 h
  5. filtrationThe suspension is filtered
  6. extractionthe filtrate extracted 3 times with AcOEt
  7. washThe organic phases are washed twice with 1 N HCl
  8. additionThe combined acidic phases are made basic by addition of saturated Na2CO3 solution
  9. extractionextracted 3 times with AcOEt
  10. washThe organic layers are washed twice with water and brine
  11. dry with materialdried (Na2SO4)
  12. concentrationconcentrated
  13. extractionColumn chromatography (SiO2; AcOEt/EtOH/NH3 95:5:1→90:10:1) followed by extraction between 3 portions of AcOEt, 3 portions of water and finally brine
  14. customdrying
  15. concentration(Na2SO4) and concentration

Sources & evidence

ORD record
ord-ee0e55d4de714a5eab3b4ae7d1837a64
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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