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Sodium Bicarbonate → 1-[1-(4-Nitrophenyl)piperidin-4-yl]-4-(oxetan-3-yl)piperazine

HRID 1526247
Notes
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Reaction equation

HRID 1526247 reaction equation
Cl.[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)([O-:4])=[O:3].[O:23]1[CH2:26][C:25](=O)[CH2:24]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C.ClCCl>[N+:2]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:12][CH2:13][CH:14]([N:17]3[CH2:22][CH2:21][N:20]([CH:25]4[CH2:26][O:23][CH2:24]4)[CH2:19][CH2:18]3)[CH2:15][CH2:16]2)=[CH:9][CH:10]=1)([O-:4])=[O:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 150242543-OxetanoneHCID 1176669641-[1-(4-Nitrophenyl)piperidin-4-yl]piperazine monohydrochloride

Product 1

HCID 1176670631-[1-(4-Nitrophenyl)piperidin-4-yl]-4-(oxetan-3-yl)piperazineYield 63.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-[1-(4-nitrophenyl)piperidin-4-yl]piperazine monohydrochloride (1 g), oxetan-3-one (300 mg), sodium triacetoxyborohydride (1.02 g), dichloromethane (20 mL), acetic acid (1 mL), and chloroform (30 mL) was stirred at room temperature for 2 days. To the reactant were added a saturated aqueous sodium hydrogen carbonate solution and chloroform, followed by liquid separation. The organic phase was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=1:0-9:1) to obtain 1-[1-(4-nitrophenyl)piperidin-4-yl]-4-(oxetan-3-yl)piperazine (670 mg) as a yellow solid.

Workup

  1. customfollowed by liquid separation
  2. washThe organic phase was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=1:0-9:1)

Sources & evidence

ORD record
ord-a8800b6858194b22ae0b926a14ade9cb
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09085540B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes