Hydrochloric Acid → HCID 20513191, compound

HRID 1163908Notes

Reaction equation

HRID 1163908 reaction equation
Cl.[CH2:2]([NH:9][CH2:10][CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(O[CH:24](OCC)[CH2:25][NH:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])C.Cl>CO.O>[CH2:30]([O:29][C:27]([NH:26][CH2:25][CH:24]1[C:13]2[NH:14][C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:12]=2[CH2:11][CH2:10][N:9]1[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:28])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 292521Benzyl 2,2-diethoxyethylcarbamateHCID 70533037N-Benzyl-2-(1H-indol-3-yl)ethan-1-amine--hydrogen chloride (1/1)

Product 1

HCID 20513191HCID 20513191, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of 50 g of N-benzyl-tryptamine hydrochloride (i.e., 3-(2-(benzylamino)-ethyl)indole hydrochloride) in 500 ml of methanol-water (4:1) are added 57.9 g of N-benzyloxycarbonyl-aminoacetaldehyde diethylacetal and 25 ml of 10% hydrochloric acid, and the mixture is refluxed for 16 hours. After the reaction, the reaction mixture is evaporated under reduced pressure to remove solvent, and the resultant crystals are collected by filtration. After being washed with water and ether, said crystals are added to a saturated sodium bicarbonate solution, and then extracted with ethyl acetate. The extract is washed with water, dried and then evaporated to remove solvent. The residue (oil, 60 g) is purified by silica gel chromatography (Solvent: chloroform-methanol (20:1)). 46 g of 1,2,3,4-tetrahydro-1-((N-benzyloxycarbonylamino)methyl)-2-benzyl-β-carboline are thereby obtained as a caramel. Yield: 62%

Workup

  1. temperaturethe mixture is refluxed for 16 hours
  2. customAfter the reaction
  3. customthe reaction mixture is evaporated under reduced pressure
  4. customto remove solvent
  5. filtrationthe resultant crystals are collected by filtration
  6. washAfter being washed with water and ether
  7. additionare added to a saturated sodium bicarbonate solution
  8. extractionextracted with ethyl acetate
  9. washThe extract is washed with water
  10. customdried
  11. customevaporated
  12. customto remove solvent
  13. customThe residue (oil, 60 g) is purified by silica gel chromatography (Solvent: chloroform-methanol (20:1))

Sources & evidence

ORD record
ord-ae08f53044ad42128a737c1846384b2b
Source dataset
uspto-grants-1983_01
Patent number
US04367230

Reaction notes

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