Water → HCID 71278618, compound

HRID 1749922Notes

Reaction equation

HRID 1749922 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=O)[C:5]([O:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:18][N:24]2[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]2)[C:5]([O:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 86682046Methyl 5-chloro-3-formyl-2-(2-methoxy-2-oxoethoxy)benzoate

Product 1

HCID 71278618HCID 71278618, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 5-chloro-3-formyl-2-(2-methoxy-2-oxoethoxy)benzoate (0.99 g, 3.5 mmol) in methylene chloride (30 mL) was added with N-methylpiperazine (0.38 g, 3.8 mmol), and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was cooled to 0° C., and then added portionwise with sodium triacetoxyborohydride (0.12 g, 5.5 mmol). After completion of the addition, the reaction mixture was warmed to room temperature, and stirred for 12 hours. The reaction mixture was added with water, the mixture was extracted with ethyl acetate, and the organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, 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→95:5)) to obtain methyl 5-chloro-2-(2-methoxy-2-oxoethoxy)-3-[(4-methylpiperazin-1-yl)methyl]benzoate (1.2 g, 75%).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. additionAfter completion of the addition
  3. temperaturethe reaction mixture was warmed to room temperature
  4. stirringstirred for 12 hours
  5. extractionthe mixture was extracted with ethyl acetate
  6. washthe organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. washthe residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (99:1→95:5))

Sources & evidence

ORD record
ord-1445c080d298441280c986846686dbaa
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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