Sulfuric Acid → HCID 67784093, compound

HRID 1755998Notes

Reaction equation

HRID 1755998 reaction equation
[CH2:1]1[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH2:4][CH2:3][NH:2]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.[CH3:14][C@@H:15]1[CH2:19]OS(=O)(=O)[N:16]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:14][C@@H:15]([NH:16][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)[CH2:19][N:2]1[CH2:3][CH2:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH2:1]1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 107838Tetrahydro-beta-carbolineHCID 516892Sodium BicarbonateHCID 22863100(R)-4-methyl-3-pyridin-2-yl[1,2,3]oxathiazolidine-2,2-dioxide

Product 1

HCID 67784093HCID 67784093, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1, 2, 3, 4-tetrahydro-9H-pyrido[3, 4-b]indole (1.7 g, 9.8 mmol) and (R)-4-methyl-3-(pyridin-2-yl)-[1, 2, 3]-oxathiazolidine-2, 2-dioxide (1.90 g, 8.9 mmol) in 30 ml of anhydrous dimethylformamide was stirred under nitrogen at room temperature for two hours. The dimethylformamide was removed under reduced pressure and the residue was dissolved in 15 ml of tetrahydrofuran plus 5 ml of water. Concentrated sulfuric acid (470 μl, 8.9 mmol) was added dropwise and the reaction stirred at room temperature for 30 minutes. Sodium bicarbonate (3.0 g, 35 mmol) is then added and the mixture stirred at room temperature overnight. The reaction was partitioned between ethyl acetate and water. The organic layer was separated. The aqueous layer was made basic with sodium bicarbonate and then extracted with ethyl acetate. The organic layers were combined, washed two times with water, dried (MgSO4) and the solvent removed under reduced pressure to give 2.68 g (98%) of (R)-[1-methyl-2-(1, 3, 4, 9-tetrahydro-2H-pyrido [3, 4-b]indol-2-yl)-ethyl]-pyridin-2-yl-amine as a light yellow oil, MS [M+HI+ 307.

Workup

  1. customThe dimethylformamide was removed under reduced pressure
  2. dissolutionthe residue was dissolved in 15 ml of tetrahydrofuran
  3. stirringthe reaction stirred at room temperature for 30 minutes
  4. stirringthe mixture stirred at room temperature overnight
  5. customThe reaction was partitioned between ethyl acetate and water
  6. customThe organic layer was separated
  7. extractionextracted with ethyl acetate
  8. washwashed two times with water
  9. dry with materialdried (MgSO4)
  10. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-887e373d509b499f832ec7698c268b1d
Source dataset
uspto-grants-1995_08
Patent number
US05439915

Reaction notes

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