Acetic Acid → 1-[3-(Ethyloxy)-4-nitrophenyl]-4-(1-methylethyl)piperazine

HRID 419541Notes

Reaction equation

HRID 419541 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH3:2].[CH3:19][C:20]([CH3:22])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CC(O)=O>ClCCCl.C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([N:13]2[CH2:14][CH2:15][N:16]([CH:20]([CH3:22])[CH3:19])[CH2:17][CH2:18]2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH3:2]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 594525801-(3-Ethoxy-4-nitrophenyl)piperazine

Product 1

HCID 594529251-[3-(Ethyloxy)-4-nitrophenyl]-4-(1-methylethyl)piperazineYield 88%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 1-[3-(ethyloxy)-4-nitrophenyl]piperazine (Example 143, step A) (0.285 g, 1.13 mmol)) and acetone (0.13 g, 2.26 mmol) was stirred in DCE (5 mL) at rt under N2. To this mixture was added sodium triacetoxyborohydride (0.60 g, 2.8 mmol) and HOAc (0.136 g, 2.26 mmol). The reaction was stirred for approximately 24 h. The reaction was diluted with DCM and aqueous (saturated) NaHCO3. The aqueous layer was extracted with DCM (2×). The combined organic layers were dried over MgSO4, filtered, concentrated, and chromatographed on silica gel to give the title compound of step A (291 mg, 0.99 mmol, 88%) as a yellow solid. MS (ESI): 294 [M+H]+.

Workup

  1. extractionThe aqueous layer was extracted with DCM (2×)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on silica gel

Sources & evidence

ORD record
ord-27928e72e31643b3bacc1bac412b06e5
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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