Acetic Acid → N-[(indol-7-yl)methyl]-2,4-dimethoxybenzylamine

HRID 910117Notes

Reaction equation

HRID 910117 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[CH:22]=O)[CH:15]=[CH:14]1.C(O)(=O)C>C1(C)C=CC=CC=1>[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[CH2:22][NH:6][CH2:5][C:4]2[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:3]=2[O:2][CH3:1])[CH:15]=[CH:14]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5972502,4-DimethoxybenzylamineHCID 2734629Indole-7-carboxaldehyde

Product 1

HCID 17985601N-[(indol-7-yl)methyl]-2,4-dimethoxybenzylamine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Add 2,4-dimethoxybenzylamine (27.64 g, 165.3 mmol) to a solution of indole-7-carboxaldehyde (20.0 g, 137.7 mmol) and acetic acid (8.26 ml, 137.7 mmol) in toluene (250 ml). Reflux and collect water using a Dean-Stark trap while replacing with fresh anhydrous toluene. Concentrate under reduced pressure, dissolve the residue in methanol and add sodium borohydride in portions. Dilute with ethyl acetate and wash sequentially with saturated aqueous sodium bicarbonate followed by saturated aqueous sodium chloride, dry over magnesium sulfate, and concentrate under reduced pressure to provide the desired compound as a brown oil.

Workup

  1. temperatureReflux
  2. customcollect water using a Dean-Stark trap
  3. concentrationConcentrate under reduced pressure
  4. dissolutiondissolve the residue in methanol
  5. additionadd sodium borohydride in portions
  6. additionDilute with ethyl acetate
  7. washwash sequentially with saturated aqueous sodium bicarbonate
  8. dry with materialdry over magnesium sulfate
  9. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-53471242cde94739b56828fcfc18a20e
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Reaction notes

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