Sulfuric acid magnesium salt (1:1) → HCID 86693005, compound

HRID 2173208Notes

Reaction equation

HRID 2173208 reaction equation
[O:1]=[C:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][CH:12]=O)=[CH:10][C:5]=2[CH2:4][O:3]1.[C:14]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].[O-]S([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[O:1]=[C:2]1[C:6]2[CH:7]=[CH:8][C:9](/[CH:11]=[CH:12]/[N:24]3[CH2:23][CH2:22][N:21]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:26][CH2:25]3)=[CH:10][C:5]=2[CH2:4][O:3]1

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 143452tert-Butyl piperazine-1-carboxylateHCID 772312612-(1-Oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehyde

Product 1

HCID 86693005HCID 86693005, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (3.5 g, 20 mmol), Boc-piperazine (3.5 g, 20 mmol) and anhydrous MgSO4(20 g, 166 mmol) in 100 mL of anhydrous DCM were stirred at room temperature over night. The solid was filtered and the solvent was evaporated at reduced pressured to get the crude product. The crude product was purified via column chromatograph to afford tert-butyl 4-[(E)-2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethenyl]piperazine-1-carboxylate. 1H-NMR (400 MHz, CDCl3) δ ppm 7.74 (d, J=8.2 Hz, 1H), 7.29˜7.34 (m, 2H), 6.88 (d, J=13 Hz, 1H), 5.55 (d, J=14 Hz, 1H), 5.25 (s, 2H), 3.49˜3.58 (m, 4H), 3.12˜3.17 (m, 4H), 1.50 (s, 9H).

Workup

  1. filtrationThe solid was filtered
  2. customthe solvent was evaporated at reduced pressured
  3. customto get the crude product
  4. customThe crude product was purified via column chromatograph

Sources & evidence

ORD record
ord-cddefaa1f4984453b743fab0b06ab7fe
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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