Triethylamine → HCID 18794227, compound

HRID 1004067Notes

Reaction equation

HRID 1004067 reaction equation
[CH3:1][C:2]1[NH:16][CH2:15][CH2:14][C:4]2=[C:5]3[C:10](=[N:11][C:3]=12)[CH:9]=[CH:8][C:7]([O:12][CH3:13])=[CH:6]3.C(N(CC)CC)C.[S:24](Cl)([CH3:27])(=[O:26])=[O:25]>ClCCl>[CH2:1]=[C:2]1[C:3]2[NH:11][C:10]3[C:5](=[CH:6][C:7]([O:12][CH3:13])=[CH:8][CH:9]=3)[C:4]=2[CH2:14][CH2:15][N:16]1[S:24]([CH3:27])(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178487038HCID 178487038, compound

Product 1

HCID 18794227HCID 18794227, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10-Methoxyharmalan (646 mg, 3 mmol) is dissolved in dry dichloromethane (40 ml). Triethylamine (1 ml, 7.2 mmol) and then, dropwise, mesyl chloride (0.25 ml, 3.2 mmol) are successively added with stirring at room temperature under a nitrogen atmosphere. The mixture is stirred for 4 hours at room temperature. Subsequently, after removal of the dichloromethane, the residue is subjected to flash chromatography on a silica column (AcOEt/PE, 50/50). 1-Methylene-2-mesyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline is thus obtained (350 mg, Y=40%).

Workup

  1. stirringThe mixture is stirred for 4 hours at room temperature
  2. customSubsequently, after removal of the dichloromethane

Sources & evidence

ORD record
ord-ed9b18c4db184868a410806acb38a6f6
Source dataset
uspto-grants-2000_04
Patent number
US06048868

Reaction notes

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