Water → 1-(3,4-Methylenedioxyphenyl)-2-(pyridin-4-yl)methyl-2,3,4,9-tetrahydro-1H-beta-carboline

HRID 2415363Notes

Reaction equation

HRID 2415363 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][NH:11]3)=[CH:4][C:3]=2[O:2]1.Cl.[N:24]1[CH:29]=[CH:28][C:27]([CH2:30]Cl)=[CH:26][CH:25]=1.C1CCN2C(=NCCC2)CC1.O>CN(C=O)C.C(OCC)(=O)C>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[CH2:30][C:27]3[CH:28]=[CH:29][N:24]=[CH:25][CH:26]=3)=[CH:4][C:3]=2[O:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 745704-(Chloromethyl)pyridinium chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2011721-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-beta-carboline

Product 1

HCID 226403141-(3,4-Methylenedioxyphenyl)-2-(pyridin-4-yl)methyl-2,3,4,9-tetrahydro-1H-beta-carboline

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(3,4-methylenedioxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline (2.92 g, 10 mmol) (prepared according to the process as disclosed in WO97/43287, Intermediate 7, page 24), 4-picolylchloride hydrochloride (1.64 g, 10 mmol) and DBU (3.1 g, 20 mmol) in DMF (50 mL) was stirred at room temperature for 16 h. Water (100 mL) and ethyl acetate (100 mL) were added to the reaction mixture. The solute, present in the organic phase, was purified by column chromatography (silica gel, ethyl acetate) to yield the product as an off-white solid.

Workup

  1. customThe solute, present in the organic phase, was purified by column chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-336a8f0a64494055b49450cc96fa8032
Source dataset
uspto-grants-2004_11
Patent number
US06818646B2

Reaction notes

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