Water → HCID 13561926, compound

HRID 1249032Notes

Reaction equation

HRID 1249032 reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH:3]([C:14]([OH:16])=[O:15])[NH:2]1.[OH-].[Na+].O.[CH2:20](Br)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].[C:31](=[S:33])=[S:32]>CS(C)=O>[CH2:20]([S:33][C:31]([N:2]1[CH:3]([C:14]([OH:16])=[O:15])[CH2:4][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[NH:12][C:13]=2[CH2:1]1)=[S:32])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

7

Reactant 5

HCID 962WaterHCID 6348Carbon DisulfideHCID 81731-BromodecaneHCID 14798Sodium HydroxideHCID 982851,2,3,4-Tetrahydro-Beta-Carboline-3-Carboxylic Acid

Product 1

HCID 13561926HCID 13561926, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In the same manner as described in Example 6, (3RS)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (4.32 g), NaOH (1.65 g), water (2 ml), dimethylsulfoxide (24 ml), carbon disulfide (1.2 ml) and n-decyl bromide (5.31 g) are reacted and treated. The residue thus obtained is purified by silica gel column chromatography (solvent, chloroform:methanol:acetic acid=98:1:0.5) and then crystallized from n-hexane to give the title compound (4.8 g, 55%), m.p. 152.5°-154° C. (decomp.).

Workup

  1. customare reacted
  2. additiontreated
  3. customThe residue thus obtained
  4. customis purified by silica gel column chromatography (solvent, chloroform:methanol:acetic acid=98:1:0.5)
  5. customcrystallized from n-hexane

Sources & evidence

ORD record
ord-1851311b1f33463d840aa16c5829c36a
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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