tert-Butyl piperazine-1-carboxylate → HCID 71278536, compound

HRID 1749906Notes

Reaction equation

HRID 1749906 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[C:3]=1[C:12]([OH:14])=O.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[C:38]([N:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1)([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39]>C(Cl)Cl.O>[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[C:3]=1[C:12]([N:48]1[CH2:47][CH2:46][N:45]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:50][CH2:49]1)=[O:14]

Participants

7

Reactant 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 86682036HCID 86682036, compound

Product 1

HCID 71278536HCID 71278536, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-carboxylic acid (0.060 g, 0.31 mmol) in methylene chloride (2.0 mL) was successively added with 1-hydroxybenzotriazole monohydrate (0.008 g, 0.052 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.086 g, 0.45 mmol), and N-Boc-piperazine (0.067 g, 0.36 mmol), and the mixture was stirred at room temperature for 14 hours. The reaction mixture was added with water, the mixture was extracted with ethyl acetate, and the organic layer was washed successively with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (99:1→90:10)) to obtain tert-butyl 4-(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-carbonyl)piperazine-1-carboxylate (0.072 g, 66%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washthe residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (99:1→90:10))

Sources & evidence

ORD record
ord-3a4fb7d5cb1b45a2aad24b3571cc9a54
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

Loading…