1-Methylpiperazine → HCID 117728791, compound

HRID 2200030Notes

Reaction equation

HRID 2200030 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:20])[C:9]=1[C:10]1[N:14]2[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:13]2=[N:12][N:11]=1)[CH:5]=O.[CH3:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][N:25]2[CH2:26][CH2:27][N:22]([CH3:21])[CH2:23][CH2:24]2)[CH:7]=[C:8]([Cl:20])[C:9]=1[C:10]1[N:14]2[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:13]2=[N:12][N:11]=1

Participants

6

Reactant 3

HCID 531671-Methylpiperazine2×HCID 5049666Sodium triacetoxyborohydride2×HCID 117729319HCID 117729319, compound

Product 1

HCID 117728791HCID 117728791, compoundYield 57.8%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A cloudy solution of Intermediate 13c (0.66 g, 1.80 mmol) in DCE (18 mL) was treated with 1-methylpiperazine (0.22 mL, 2.00 mmol) then sodium triacetoxyborohydride (0.58 g, 2.70 mmol), and the solution was stirred at ambient temperature overnight. The mixture was treated with another portion of 1-methylpiperazine (0.22 mL, 2.00 mmol) and sodium triacetoxyborohydride (0.58 g, 2.70 mmol), and stirred for 5 h. The mixture was cautiously diluted with a saturated aqueous sodium bicarbonate solution and the layers were separated. The aqueous layer was then extracted with DCM (2×). The combined organic layers were washed with a saturated aqueous sodium bicarbonate solution and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was dissolved in DCM and purified by FCC, using 0-8% [2M NH3 in MeOH] in DCM, to give the title compound (0.41 g, 57%). LCMS (Method 3): Rt 2.11 min, m/z 394, 396 [MH+].

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was then extracted with DCM (2×)
  3. washThe combined organic layers were washed with a saturated aqueous sodium bicarbonate solution and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. dissolutionThe residue was dissolved in DCM
  8. custompurified by FCC

Sources & evidence

ORD record
ord-8a7c168e65674ba386e9e18a0e9e87a9
Source dataset
uspto-grants-2016_06
Patent number
US09359354B2

Reaction notes

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