Acetic Acid → 1-(3-Nitropyridin-4-yl)-4-(tetrahydrofuran-3-yl)piperazine

HRID 524869Notes

Reaction equation

HRID 524869 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)([O-:3])=[O:2].[O:16]1[CH2:20][CH2:19][C:18](=O)[CH2:17]1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CC#N>[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][N:13]([CH:18]2[CH2:19][CH2:20][O:16][CH2:17]2)[CH2:12][CH2:11]1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5293923-OxotetrahydrofuranHCID 5049666Sodium triacetoxyborohydrideHCID 431140711-(3-Nitropyridin-4-yl)piperazine

Product 1

HCID 867209281-(3-Nitropyridin-4-yl)-4-(tetrahydrofuran-3-yl)piperazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A round-bottomed flask was charged with 1-(3-nitro-4-pyridyl)piperazine (prepared according to methods similar to the one depicted in Step 1 of Preparation N-1), dihydrofuran-3(2H)-one (98 mg, 1.13 mmol) and acetic acid (129 uL, 2.27 mmol) in MeCN (4 mL). Na(OAc)3BH (482.4 mg, 2.27 mmol) was added and the reaction mixture was stirred at RT for 1 h. The reaction mixture was partitioned between EtOAC and an aqueous saturated solution of Na2CO3. The organic extracts were dried over MgSO4, and concentrated under reduced pressure to give 1-(3-nitropyridin-4-yl)-4-(tetrahydrofuran-3-yl)piperazine as a yellow solid. MS (ES+) 279.1.

Workup

  1. customprepared
  2. customThe reaction mixture was partitioned between EtOAC
  3. dry with materialThe organic extracts were dried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9eb603354edf4f0aa6b212e88fc2a0e5
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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