Water → tert-Butyl 4-(3-formylpyridin-2-yl)piperazine-1-carboxylate

HRID 361792Notes

Reaction equation

HRID 361792 reaction equation
Br[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C(N(C(C)C)CC)(C)C.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].O>C1COCC1>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][N:29]([C:2]2[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 47149512-Bromonicotinaldehyde

Product 1

HCID 24741846tert-Butyl 4-(3-formylpyridin-2-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 2-bromo-3-formylpyridine (XVI, EXAMPLE 1, 2.0 g, 10.80 mmol), and diisopropylethylamine (1.39 g, 10.80 mmol) in THF is added 1-(tert-butoxycarbonyl)-piperazine (Aldrich, 2.01 g, 10.80 mmol). The mixture is heated in a sealed tube at 100° for 16 hr, cooled to 20°-25° and poured into water (100 ml). The aqueous layer is extracted with ethyl acetate (100 ml), the organic layer separated, dried over sodium sulfate and solvent evaporated to dryness. The residue is purified via flash column chromatography (silica gel; hexane/ethyl acetate (4/1)) to give the title compound, mp 88°-89°; NMR (CDCl3) 1.48, 3.42, 3.60, 6.96, 8.01, 8.39 and 10.03δ; MS (EI, m/e) 291 (M+).

Workup

  1. temperatureThe mixture is heated in a sealed tube at 100° for 16 hr
  2. temperaturecooled to 20°-25°
  3. extractionThe aqueous layer is extracted with ethyl acetate (100 ml)
  4. customthe organic layer separated
  5. dry with materialdried over sodium sulfate and solvent
  6. customevaporated to dryness
  7. customThe residue is purified via flash column chromatography (silica gel; hexane/ethyl acetate (4/1))

Sources & evidence

ORD record
ord-d4b135255f3e45f284f8f20b443a9de3
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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