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Sodium hydride → 2-(cyclopropylmethyl)-8-(1-isopropylpiperidin-4-yloxy)-3,4-dihydropyrazino[1,2-a]indol-1(2H)-one

HRID 2105356
Notes
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Reaction equation

HRID 2105356 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:19]=[CH:18][C:17]3[N:16]4[CH2:20][CH2:21][NH:22][C:23](=[O:24])[C:15]4=[CH:14][C:13]=3[CH:12]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:28][CH:29]1[CH2:31][CH2:30]1.[Cl-].[NH4+]>CN(C)C=O>[CH:29]1([CH2:28][N:22]2[CH2:21][CH2:20][N:16]3[C:17]4[CH:18]=[CH:19][C:11]([O:10][CH:7]5[CH2:8][CH2:9][N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6]5)=[CH:12][C:13]=4[CH:14]=[C:15]3[C:23]2=[O:24])[CH2:31][CH2:30]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 81503BromomethylcyclopropaneHCID 166795188-(1-isopropylpiperidin-4-yloxy)-3,4-dihydropyrazino[1,2-a]indol-1(2H)-one

Product 1

HCID 529412692-(cyclopropylmethyl)-8-(1-isopropylpiperidin-4-yloxy)-3,4-dihydropyrazino[1,2-a]indol-1(2H)-oneYield 38%

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

Procedure

To the solution of 0.15 g (0.46 mmol) 8-(1-isopropyl-piperidin-4-yloxy)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one (example 1) in 3 mL N,N-dimethylformamide, 24 mg (0.55 mmol, 55% dispersion in mineral oil) sodium hydride was added. After 30 min., 1-(bromomethyl)cyclopropane was added and the mixture was stirred until completion of the reaction as indicated by TLC (2 h). The reaction mixture was poured on 10% aqueous ammonium chloride solution and was extracted three times with ethyl acetate. The organic layers were washed with water and brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography on silica gel with dichloromethane:methanol:ammonia (9:1:0.1 v/v) to give the desired compound as a white solid (38%).

Workup

  1. customas indicated by TLC (2 h)
  2. extractionwas extracted three times with ethyl acetate
  3. washThe organic layers were washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash column chromatography on silica gel with dichloromethane:methanol:ammonia (9:1:0.1 v/v)

Sources & evidence

ORD record
ord-ffa135858d7242a8a6dbe95c70e15d66
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07579351B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes