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Benzyl Bromide → 1-benzyl-2-methyl-2,3-dihydro-1H-indole

HRID 346842
Notes
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Reaction equation

HRID 346842 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.C([O-])([O-])=O.[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[NH4+].[Cl-]>CN(C=O)C.CCOCC>[CH2:17]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:10][CH:2]1[CH3:1])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 233052-MethylindolineHCID 25517Ammonium Chloride

Product 1

HCID 105135891-benzyl-2-methyl-2,3-dihydro-1H-indoleYield 101.5%

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1 g (7.5 mmol) of 2-methyl-2,3-dihydro-1H-indole in anhydrous DMF were added 1.03 g (7.5 mmol) of K2CO3 and then dropwise 0.97 mL (8.0 mmol) of benzylbromide. The mixture was stirred at RT for 3hrs and then distributed between Et2O and a saturated aqueous solution of NH4Cl. The combined organic phases were dried over Na2SO4 and evaporated to yield 1.7 g (quantitative) of crude 1-benzyl-2-methyl-2,3-dihydro-1H-indole, light blue oil, MS: 224 (MH+).

Workup

  1. dry with materialThe combined organic phases were dried over Na2SO4
  2. customevaporated

Sources & evidence

ORD record
ord-2a2f6613161d4ab09e81152c621626b0
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07173048B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes