Ethanol → HCID 20513162, compound

HRID 1163910Notes

Reaction equation

HRID 1163910 reaction equation
[CH2:1]([N:5]([C:17](=O)[CH2:18][NH:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)(Cl)=O.C(O)C.[BH4-].[Na+]>C1(C)C=CC=CC=1.O>[CH2:23]([O:22][C:20]([NH:19][CH2:18][CH:17]1[C:9]2[NH:10][C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8]=2[CH2:7][CH2:6][N:5]1[CH2:1][CH2:2][CH2:3][CH3:4])=[O:21])[CH3:24]

Participants

7

Reactant 4

HCID 702EthanolHCID 24813Phosphorus oxychlorideHCID 4311764Sodium borohydrideHCID 20513208HCID 20513208, compound

Product 1

HCID 20513162HCID 20513162, compoundYield 77.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 3.40 g of N-n-butyl-N-(N-ethoxycarbonylglycyl)-tryptamine in 40 ml of anhydrous toluene are added 10 ml of phosphorus oxychloride, and the mixture is stirred at 120° C. for 45 minutes. The mixture is condensed under reduced pressure, and 100 ml of ethanol are added to the residue. Then, sodium borohydride is added to the mixture until said mixture becomes alkaline, and the mixture is stirred at room temperature for 30 minutes. After the reaction, the reaction mixture is condensed, and water is added to the residue. The aqueous mixture is extracted with chloroform, and the extract is washed, dried and then evaporated to remove solvent. The residue (oil, 4.0 g) thus obtained is purified by silica gel chromatography (Solvent: chloroform-ethyl acetate (1:1)). 2.50 g of 1,2,3,4-tetrahydro-1-((N-ethoxycarbonylamino)methyl)-2-n-butyl-β-carboline are thereby obtained as a pale yellow oil. Yield: 77.6% The physico-chemical properties of this product are identical with those of the product obtained in Example 3.

Workup

  1. additionare added to the residue
  2. stirringthe mixture is stirred at room temperature for 30 minutes
  3. customAfter the reaction
  4. additionis added to the residue
  5. extractionThe aqueous mixture is extracted with chloroform
  6. washthe extract is washed
  7. customdried
  8. customevaporated
  9. customto remove solvent
  10. customThe residue (oil, 4.0 g) thus obtained
  11. customis purified by silica gel chromatography (Solvent: chloroform-ethyl acetate (1:1))

Sources & evidence

ORD record
ord-b326fb3c295f4a4dadd3c2374d696fd2
Source dataset
uspto-grants-1983_01
Patent number
US04367230

Reaction notes

Loading…