Triethylamine → HCID 71278709, compound

HRID 1749723Notes

Reaction equation

HRID 1749723 reaction equation
Br[CH2:2][C:3]1[C:11]2[O:10][CH2:9][C:8](=[O:12])[C:7]=2[CH:6]=[C:5]([O:13][CH3:14])[CH:4]=1.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C>C(Cl)Cl>[CH3:14][O:13][C:5]1[CH:4]=[C:3]([CH2:2][N:25]2[CH2:24][CH2:23][N:22]([C:20]([O:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:21])[CH2:27][CH2:26]2)[C:11]2[O:10][CH2:9][C:8](=[O:12])[C:7]=2[CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 86681918HCID 86681918, compound

Product 1

HCID 71278709HCID 71278709, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-(bromomethyl)-5-methoxybenzofuran-3(2H)-one (0.040 g, 0.16 mmol) in methylene chloride (2.0 mL) was added with 1-tert-butoxycarbonylpiperazine (0.032 g, 0.17 mmol), and triethylamine (0.021 g, 0.20 mmol), and the mixture was stirred at room temperature for 5 hours. The solvent was evaporated under reduced pressure, and then the residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (95:5)) to obtain tert-butyl 4-[(5-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.008 g, 14%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washthe residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (95:5))

Sources & evidence

ORD record
ord-5ca213eb77b9445b8c17b651f4c14fc6
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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