Benzyl Bromide → 1-(3,4-Methylenedioxyphenyl)-2-benzyl-2,3,4,9-tetrahydro-1H-beta-carboline

HRID 988299Notes

Reaction equation

HRID 988299 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.C(N(CC)CC)C.[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[OH-].[Na+]>CN(C=O)C.O>[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:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:4][C:3]=2[O:2]1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 2011721-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-beta-carboline

Product 1

HCID 129930141-(3,4-Methylenedioxyphenyl)-2-benzyl-2,3,4,9-tetrahydro-1H-beta-carboline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the 1-(3,4-methylenedioxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline (prepared according to the process as disclosed in WO97/43287, Intermediate 7, page 24) (7.37 g, 25 mmol) in dry DMF (25 mL) was added triethylamine (3.52 mL, 25 mmol) and benzyl bromide (3.00 mL, 25 mmol). The mixture was stirred at ambient temperature overnight and added dropwise to a solution of sodium hydroxide (25 mmol) in water (200 mL). A precipitate was formed, collected by vacuum filtration, washed with water (2×50 mL), and dried in vacuo overnight to yield the product as a freely flowing pale yellow powder.

Workup

  1. customA precipitate was formed
  2. filtrationcollected by vacuum filtration
  3. washwashed with water (2×50 mL)
  4. customdried in vacuo overnight
  5. customto yield the product as

Sources & evidence

ORD record
ord-9519693c64b34b2e9136649f72b6a850
Source dataset
uspto-grants-2003_10
Patent number
US06635638B2

Reaction notes

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