Ethanolamine → HCID 86603036, compound

HRID 855233Notes

Reaction equation

HRID 855233 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:13]([CH2:15][NH2:16])[OH:14].[BH4-].[Na+].[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][C:26]=2[C:28](O)=[O:29])[CH:21]=[CH:20]1.CCN=C=NCCCN(C)C.Cl>CO>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][N:16]([CH2:15][CH2:13][OH:14])[C:28]([C:26]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:27]=2[NH:19][CH:20]=[CH:21]3)=[O:29])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 700EthanolamineHCID 703244-tert-ButylbenzaldehydeHCID 742811H-Indole-7-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 86603036HCID 86603036, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.24 g (20 mmol) of 4-tert-butyl benzaldehyde and 1.22 g (20 mmol) of ethanol amine were dissolved in 20 ml methanol and stirred at rt for 30 min. 740 mg (20 mmol) of sodium borohydride were added in portions under nitrogen and the reaction mixture was stirred for 1 h at rt after complete addition. The solvent was evaporated and the residue was dissolved in diethyl ether. The organic layer was washed twice with water, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was dissolved in 20 ml DCM and 3.22 g (20 mol) of 1H-indole-7-carboxylic acid and 3.82 g (20 mmol) of EDC.HCl were added. The reaction mixture was stirred at rt over night. The solvent was evaporated and the residue was dissolved in EtOAc. The organic layer was washed twice with 1N aqueous HCl solution, once with 2N aqueous NaOH solution and once with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated to leave a colorless oil, which on treatment with diethyl ether yielded 2.54 g (36%) product as a white solid after filtration and drying. MS (ISP) 351.3 (M+H)+.

Workup

  1. stirringthe reaction mixture was stirred for 1 h at rt
  2. additionafter complete addition
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in diethyl ether
  5. washThe organic layer was washed twice with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. dissolutionThe residue was dissolved in 20 ml DCM
  10. stirringThe reaction mixture was stirred at rt over night
  11. customThe solvent was evaporated
  12. dissolutionthe residue was dissolved in EtOAc
  13. washThe organic layer was washed twice with 1N aqueous HCl solution, once with 2N aqueous NaOH solution and once with saturated aqueous NaCl solution
  14. dry with materialdried over sodium sulfate
  15. filtrationfiltered
  16. customthe solvent was evaporated
  17. customto leave a colorless oil, which on treatment with diethyl ether

Sources & evidence

ORD record
ord-ac4c8b9c307d4267b3ac0a896eba1283
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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