Acetic Acid → HCID 62998053, compound

HRID 557193Notes

Reaction equation

HRID 557193 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].[NH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[CH:14]=O)[CH:7]=[CH:6]1.C(O)(=O)C.[BH4-].[Na+]>C1(C)C=CC=CC=1.CO.O>[NH:4]1[C:14]2[C:3](=[CH:9][CH:10]=[CH:11][C:12]=2[CH2:13][NH:5][CH2:6][CH2:7][CH3:8])[CH:2]=[CH:1]1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 7852PropylamineHCID 2734629Indole-7-carboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 62998053HCID 62998053, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Add propyl amine (3.66 g, 62.07 mmol) to a solution of indole-7-carboxaldehyde (3.0 g, 20.68 mmol) and acetic acid (2.65 ml, 41.3 mmol) in toluene (100 ml). Heat at reflux constantly removing water with a Dean Stark apparatus. Concentrate the reaction under reduced pressure and re-dissolve in methanol. Gently add sodium borohydride (0.39 g, 10.34 mmol). Stir for 1 hour at room temperature, concentrate, and partition between ethyl acetate and saturated aqueous sodium bicarbonate. Concentrate the organic layers under reduced pressure. Compound carried onto next step without purification.

Workup

  1. temperatureHeat
  2. concentrationConcentrate
  3. customthe reaction under reduced pressure
  4. concentrationconcentrate
  5. custompartition between ethyl acetate and saturated aqueous sodium bicarbonate
  6. concentrationConcentrate the organic layers under reduced pressure
  7. customCompound carried onto next step without purification

Sources & evidence

ORD record
ord-2a959fd1bb5f4a8f99220133bf64f40c
Source dataset
uspto-grants-2011_11
Patent number
US08058425B2

Reaction notes

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