4-[4-(tert-Butoxycarbonyl)piperazin-1-yl]benzyl alcohol → Tert-butyl 4-(4-formylphenyl)piperazine-1-carboxylate

HRID 1459432Notes

Reaction equation

HRID 1459432 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1>O=[Mn]=O.C(Cl)(Cl)Cl>[CH3:20][C:18]([CH3:21])([O:17][C:15]([N:12]1[CH2:11][CH2:10][N:9]([C:6]2[CH:5]=[CH:4][C:3]([CH:2]=[O:1])=[CH:8][CH:7]=2)[CH2:14][CH2:13]1)=[O:16])[CH3:19]

Participants

4

Reactant 1

HCID 27955104-[4-(tert-Butoxycarbonyl)piperazin-1-yl]benzyl alcohol2×

Product 1

HCID 2795509Tert-butyl 4-(4-formylphenyl)piperazine-1-carboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

To a 50 mL round bottomed flask with a stirring bar and an argon inlet was added 1-hydroxymethyl-4-(4-(1,1-dimethylethoxycarbonyl)piperazinyl)benzene, 35-1 (2.15 g, 7.35 mmol), CHCl3 (100 mL), and MnO2 (12.0 g, 138 mmol). This mixture was stirred at ambient temperature for 24 h. The salts were removed by filtration and the solvent was removed in vacuo. The residue was chromatographed on 90 g of silica gel using 30/70 EtOAc-hexane as eluant. There was obtained 4-(4-(1,1-dimethylethoxycarbonyl)piperazinyl)benzaldehyde 35-2 (2.10 g, 99%) as a crystalline solid. 1H NMR (CDCl3): δ 1.49 (s, 9H), 3.39 (m, 4H), 3.59 (m, 4H), 6.89 (d, J=9 Hz, 2H), 7.75 (d, J=9 Hz, 2H), 9.79 (s, 1H).

Workup

  1. customThe salts were removed by filtration
  2. customthe solvent was removed in vacuo
  3. customThe residue was chromatographed on 90 g of silica gel using 30/70 EtOAc-hexane as eluant

Sources & evidence

ORD record
ord-d76225eb82484029af82fc103d980bba
Source dataset
uspto-grants-1998_12
Patent number
US05854245

Reaction notes

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