1-Ethylpiperazine → 1-(1-(Diphenylmethyl)azetidin-3-yl)-4-ethylpiperazine

HRID 707501Notes

Reaction equation

HRID 707501 reaction equation
[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]2[CH2:11][C:10](=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:19]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[CH3:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O.C(O)(=O)C>[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]2[CH2:11][CH:10]([N:24]3[CH2:25][CH2:26][N:21]([CH2:19][CH3:20])[CH2:22][CH2:23]3)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 791961-EthylpiperazineHCID 516892Sodium BicarbonateHCID 37355581-(Diphenylmethyl)azetidin-3-oneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 1181624801-(1-(Diphenylmethyl)azetidin-3-yl)-4-ethylpiperazineYield 89%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixed solution of a commercially available product of 1-(diphenylmethyl)azetidin-3-one (10.1 g, 42.6 mmol), TH-IF (100 mL) and acetic acid (5.00 mL) was added ethylpiperazine (6.48 mL, 51.1 mmol) at room temperature. The resultant mixture was stirred at room temperature for 45 minutes. Sodium triacetoxyborohydride (18.1 g, 85.1 mmol) was added to the reaction mixture at room temperature and then stirred at room temperature for 15 hours. Sodium hydrogen carbonate and water were added to the reaction mixture, and the resultant solution was then extracted with ethyl acetate. An organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate, and then filtrated. The solvent was evaporated under a reduced pressure, and the resultant residue was purified by silica gel column chromatography (ethyl acetate-methanol) and was then further purified by NH silica gel column chromatography (heptane:ethyl acetate=2:1 and the 1:1) to give the title compound (12.7 g, yield: 89%).

Workup

  1. extractionthe resultant solution was then extracted with ethyl acetate
  2. washAn organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. customThe solvent was evaporated under a reduced pressure
  6. customthe resultant residue was purified by silica gel column chromatography (ethyl acetate-methanol)
  7. customwas then further purified by NH silica gel column chromatography (heptane

Sources & evidence

ORD record
ord-954301a3cd454305a47c4d9715e72dd1
Source dataset
uspto-grants-2015_11
Patent number
US09174998B2

Reaction notes

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