Ethanol → HCID 13561933, compound

HRID 1249042Notes

Reaction equation

HRID 1249042 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+].C(O)C.[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Cl)=[CH:25][CH:24]=1.[C:31](=[S:33])=[S:32]>>[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][S:33][C:31]([N:2]2[CH:3]([C:14]([OH:16])=[O:15])[CH2:4][C:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[NH:12][C:13]=3[CH2:1]2)=[S:32])=[CH:25][CH:24]=1

Participants

6

Reactant 5

HCID 702EthanolHCID 6348Carbon DisulfideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 14798Sodium HydroxideHCID 982851,2,3,4-Tetrahydro-Beta-Carboline-3-Carboxylic Acid

Product 1

HCID 13561933HCID 13561933, compoundYield 65%

Procedure

In the same manner as described in Example 16, (3RS)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (1.08 g), 2N NaOH (5 ml), 50% ethanol (15 ml), carbon disulfide (0.3 ml) and 4-chlorobenzyl chloride (1.13 g) are reacted and treated. The product is purified by silica gel column chromatography (solvent, chloroform:methanol:acetic acid=97:2:1) to give the title compound (1.36 g, 65%), as pale yellow powder.

Workup

  1. customare reacted
  2. additiontreated
  3. customThe product is purified by silica gel column chromatography (solvent, chloroform:methanol:acetic acid=97:2:1)

Sources & evidence

ORD record
ord-3fbb3553888747b2839cb132b384351a
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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