Formaldehyde → 3-[(4-methylpiperazin-1-yl)methyl]-1H-indole

HRID 254189Notes

Reaction equation

HRID 254189 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH3:10][N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.[CH2:17]=O>ClCCl>[CH3:10][N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 798IndoleHCID 531671-Methylpiperazine

Product 1

HCID 2275843-[(4-methylpiperazin-1-yl)methyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a three necked round bottom flask equipped with pressure equalizing funnel, indole (1.17 g, 0.01 mole) and dichloromethane (8 mL) were taken. 1-Methylpiperazine (1.01 g, 0.011 moles) and formaldehyde (9 mL, 0.012 mole) was added slowly at room temperature and the reaction mixture was stirred well for one hour. After the completion of reaction (TLC), the product was isolated by distillation under reduced pressure. The residue was extracted with ethyl acetate (2×25 mL). The combined organic extracts were washed with water, followed by brine, dried over anhydrous sodium sulfate. The organic layer was evaporated under vacuum. The residue could either be an oily liquid or solid mass. The oily mass was triturated with n-hexane to obtain a solid material. The solid obtained was identified by IR, NMR and mass spectral analyses.

Workup

  1. customIn a three necked round bottom flask equipped with pressure
  2. customAfter the completion of reaction (TLC)
  3. customthe product was isolated by distillation under reduced pressure
  4. extractionThe residue was extracted with ethyl acetate (2×25 mL)
  5. washThe combined organic extracts were washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe organic layer was evaporated under vacuum
  8. customThe oily mass was triturated with n-hexane
  9. customto obtain a solid material
  10. customThe solid obtained

Sources & evidence

ORD record
ord-f91cdf5d70774916aca3c0f30b8af2e5
Source dataset
uspto-grants-2011_01
Patent number
US07875605B2

Reaction notes

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