Acetic Acid → HCID 58976363, compound

HRID 1011259Notes

Reaction equation

HRID 1011259 reaction equation
C(O[C:4]1(O[Si](C)(C)C)[CH2:6][CH2:5]1)C.[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[CH:17][CH:16]=1)([O-:14])=[O:13].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH:4]1([N:24]2[CH2:25][CH2:26][N:21]([C:18]3[CH:17]=[CH:16][C:15]([N+:12]([O-:14])=[O:13])=[CH:20][CH:19]=3)[CH2:22][CH2:23]2)[CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 804471-(4-Nitrophenyl)piperazineHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 58976363HCID 58976363, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
62.5 °C

Procedure

A mixture of [(1-ethoxycyclopropyl)oxy]trimethylsilane (4.5 mL. 22.4 mmol, 2 eq.), 1-(4-nitrophenyl)piperazine (2.32 g, 11.1 mmol, acetic acid (6.4 mL, 5 eq.), molecule sieves (3 A, 5 g), and sodium cyanoborohydride (2.1 g, 33.3 mmol, 3 eq.) in dry methanol (50 mL) is heated at 60-65° C. for 4 h. The reaction mixture is filtered, and the filtration is evaporated. The residue is dissolved in DCM (200 mL) and the resulting solution is washed with 2 N NaOH (100 mL), brine (100 mL×2), dried over MgSO4, and evaporated to provide a yellow solid (2.75 g, 100%). The compound is used in the next reaction without further purification. 1H NMR (300 MHz, DMSO-d6), δ 8.02 (d, J=9.6 Hz, 2H), 7.00 (d, J=9.6 Hz, 2H), 3.38-3.42 (m, 4H), 2.60-2.68 (m, 4H), 1.60-1.67 (m, 1H), 0.40-0.46 (m, 2H), 0.35-0.38 (m, 2H). LCMS-ESI (m/z): calcd for C13H17N3O2, 247.1; [M+H]+ found, 248.4.

Workup

  1. filtrationThe reaction mixture is filtered
  2. filtrationthe filtration
  3. customis evaporated
  4. dissolutionThe residue is dissolved in DCM (200 mL)
  5. washthe resulting solution is washed with 2 N NaOH (100 mL), brine (100 mL×2)
  6. dry with materialdried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-ca74794762c342f8b887e7b34b68ac8c
Source dataset
uspto-grants-2011_07
Patent number
US07977352B2

Reaction notes

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