Water → Tert-butyl 4-(4-formyl-2-methoxyphenyl)piperazine-1-carboxylate

HRID 336832

Reaction equation

HRID 336832 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11].[N:12]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([N:15]2[CH2:14][CH2:13][N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16]2)=[C:3]([O:10][CH3:11])[CH:4]=1)=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27373584-Fluoro-3-methoxybenzaldehyde

Product 1

HCID 86671380Tert-butyl 4-(4-formyl-2-methoxyphenyl)piperazine-1-carboxylateYield 51%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

To 400 mg (2.60 mmol) of 4-fluoro-3-methoxybenzaldehyde diluted in 10 ml of dimethylsulfoxide are respectively added 483 mg (2.60 mmol) of tert-butyl piperazine-1-carboxylate, then 394 mg (2.85 mmol) of potassium carbonate. The solution is heated to 90° C. for 40 h, then water is added and the product is extracted several times with ethyl acetate. The organic phases are combined, dried over magnesium sulfate, and concentrated. The residue obtained is purified by chromatography on silica (cyclohexane/ethyl acetate eluent: 8:2) to yield 425 mg of tert-butyl 4-(4-formyl-2-methoxyphenyl)piperazine-1-carboxylate in the form of a colourless oil.

Workup

  1. extractionthe product is extracted several times with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue obtained
  5. customis purified by chromatography on silica (cyclohexane/ethyl acetate eluent: 8:2)

Sources & evidence

ORD record
ord-d758faf30d914d1d943e1c7686ed1efc
Source dataset
uspto-grants-2014_11
Patent number
US08889711B2

Linked notes

Loading…