Methyl iodide → HCID 86741018, compound

HRID 65078Notes

Reaction equation

HRID 65078 reaction equation
[CH2:1]([C@H:4]1[C:16]2[NH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH2:7][C@H:6]([CH2:17][OH:18])[NH:5]1)[CH2:2][CH3:3].C(N(CC)CC)C.[C:26](=[S:28])=[S:27].[CH3:29]I>CS(C)=O>[CH2:1]([C@H:4]1[C:16]2[NH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH2:7][C@H:6]([CH2:17][OH:18])[N:5]1[C:26]([S:28][CH3:29])=[S:27])[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 86741019(1RS, 3SR)-trans-1-propyl-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline

Product 1

HCID 86741018HCID 86741018, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In the same manner as described in Example 39 by using (1RS, 3SR)-trans-1-propyl-3-hydroxymethyl-1,2,3,4-tetrahydro-β-carboline (1.18 g), triethylamine (0.98 g), CS2 (0.74 g), methyl iodide (1.37 g) and dimethylsulfoxide (23 ml), there is prepared the title compound (720 mg, 44%) as white powder, NMR (CDCl3, δ): 2.70 (s, 3H, CSSCH3); Mass m/e: 334 (M+), 286 (M+ --CH3SH).

Sources & evidence

ORD record
ord-5a2c4ade8d18430aba0b0f4078cc5221
Source dataset
uspto-grants-1986_09
Patent number
US04612317

Reaction notes

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