1-Hydroxybenzotriazole → HCID 59429634, compound

HRID 505157Notes

Reaction equation

HRID 505157 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:23][CH2:22][N:11]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[C:18]([C:19]([OH:21])=O)=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.[Cl-].[NH4+]>[C:1]([O:5][C:6]([N:8]1[CH2:23][CH2:22][N:11]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[C:18]([C:19]([N:35]3[CH2:36][CH2:37][CH:32]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=4[O:25][CH3:24])[CH2:33][CH2:34]3)=[O:21])=[C:10]2[CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 5447384-(2-Methoxyphenyl)piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59657524HCID 59657524, compound

Product 1

HCID 59429634HCID 59429634, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 0.10 g (0.32 mmol) 3,4-dihydro-1H-pyrazino[1,2-a]indole-2,10-dicarboxylic acid 2-tert-butyl ester, 0.067 g (0.35 mmol) 4-(2-methoxyphenyl)-piperidine and 0.051 g (0.38 mmol) 1-hydroxybenzotriazole in 3.5 ml N,N-dimethylformamide were added 0.073 g (0.38 mmol) N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride at room temperature. After stirring for 3 h the reaction mixture was diluted with saturated aqueous ammonium chloride solution and extracted with tert-butyl methyl ether (2×50 ml). The combined organic layers were washed with 1 M sodium hydroxide solution (1×30 ml) and water (1×30 ml), dried over sodium sulfate, concentrated in vacuo and purified by flash-chromatography (aminopropyl-modified silica gel, n-heptane/ethyl acetate) to give the title compound (0.087 g, 56%) as a light yellow solid.

Workup

  1. extractionextracted with tert-butyl methyl ether (2×50 ml)
  2. washThe combined organic layers were washed with 1 M sodium hydroxide solution (1×30 ml) and water (1×30 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. custompurified by flash-chromatography (aminopropyl-modified silica gel, n-heptane/ethyl acetate)

Sources & evidence

ORD record
ord-3a27a53d31c7404f86ff143456a82eac
Source dataset
uspto-grants-2010_08
Patent number
US07781436B2

Reaction notes

Loading…