Acetic Acid → HCID 58976363, compound

HRID 1179236Notes

Reaction equation

HRID 1179236 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(O)(=O)C.C(O[C:23]1(O[Si](C)(C)C)[CH2:25][CH2:24]1)C.C([BH3-])#N.[Na+]>CO>[CH:23]1([N:13]2[CH2:14][CH2:15][N:10]([C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=3)[CH2:11][CH2:12]2)[CH2:25][CH2:24]1

Participants

6

Reactant 4

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

Product 1

HCID 58976363HCID 58976363, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(4-nitrophenyl)piperazine (1.04 g, 5.00 mmol) in methanol (25 mL) under nitrogen was added molecular sieves (1.0 g), acetic acid (3.00 g, 2.86 mL, 50.0 mmol), [(1-ethoxycyclopropyl)oxy]trimethylsilane (5.22 g, 5.99 mL, 30.0 mmol), sodium cyanoborohydride (1.41 g, 22.5 mmol). The mixture was stirred at room temperature for 2.5 d, filtered, and concentrated. To the residue was added water and 1N aq. NaOH to adjust the PH>11. The mixture was extracted ethyl acetate, and the organic layer was dried over Na2SO4, concentrated to give the title compound (1.24 g, 100%) as a yellow solid. MS (ES+): m/z=247.8.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. additionTo the residue was added water and 1N aq. NaOH
  4. extractionThe mixture was extracted ethyl acetate
  5. dry with materialthe organic layer was dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4a4dd6c6bd7a4b80a2b7a4e8491f4cd8
Source dataset
uspto-grants-2007_10
Patent number
US07279469B2

Reaction notes

Loading…