2-Methylpiperazine → 3-methyl-6-[2-(3-methylpiperazin-1-yl)ethyl]-3,4-dihydro-1H-isochromen-1-one

HRID 2173147Notes

Reaction equation

HRID 2173147 reaction equation
[CH3:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:12][CH:13]=O)[CH:9]=2)[C:4](=[O:15])[O:3]1.[CH3:16][CH:17]1[CH2:22][NH:21][CH2:20][CH2:19][NH:18]1.C([BH3-])#N.[Na+]>C(Cl)Cl>[CH3:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:12][CH2:13][N:21]3[CH2:20][CH2:19][NH:18][CH:17]([CH3:16])[CH2:22]3)[CH:9]=2)[C:4](=[O:15])[O:3]1

Participants

5

Reactant 3

HCID 660572-MethylpiperazineHCID 5003444Sodium cyanoborohydrideHCID 77230694(3-methyl-1-oxo-3,4-dihydro-1H-isochromen-6-yl)acetaldehyde

Product 1

HCID 772306783-methyl-6-[2-(3-methylpiperazin-1-yl)ethyl]-3,4-dihydro-1H-isochromen-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Freshly prepared (3-methyl-1-oxo-3,4-dihydro-1H-isochromen-6-yl)acetaldehyde was dissolved in DCM. To the solution was added 2-methyl piperazine (221 mg, 2.2 mmol) followed by sodium cyanoborohydride (165 mg, 2.64 mmol). The reaction mixture was allowed to stir overnight before being quenched with 10 mL of 1N HCl followed by stirring for 30 minutes. The reaction mixture was then treated with 50 mL of saturated sodium bicarbonate solution and extracted with DCM (3×50 mL). The combined organic layers were washed with water and brine, dried with magnesium sulfate, filtered, concentrated and purified via MPLC (30-100% (10% IPA in DCM/DCM) to afford 3-methyl-6-[2-(3-methylpiperazin-1-yl)ethyl]-3,4-dihydro-1H-isochromen-1-one. LC-MS (IE, m/z): 289 [M+1]+.

Workup

  1. custombefore being quenched with 10 mL of 1N HCl
  2. stirringby stirring for 30 minutes
  3. additionThe reaction mixture was then treated with 50 mL of saturated sodium bicarbonate solution
  4. extractionextracted with DCM (3×50 mL)
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified via MPLC (30-100% (10% IPA in DCM/DCM)

Sources & evidence

ORD record
ord-1a9ba15e72bb4d07b06f0e2399f31c11
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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