Benzyl Bromide → 1-benzylindoline

HRID 1724014Notes

Reaction equation

HRID 1724014 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[NH4+].[Cl-]>CN(C=O)C.CCOCC>[CH2:16]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 10328IndolineHCID 11430Potassium CarbonateHCID 25517Ammonium Chloride

Product 1

HCID 108050961-benzylindolineYield 69.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5 g (41.96 mmol) of indoline in DMF was treated with 5.8 g (41.96 mmol) of K2CO3 and then at 0° C. dropwise, under intense stirring, with 5.5 mL (46.2 mmol) of benzylbromide. The mixture was stirred at RT for 10 hrs and then for 2 hrs at 60° C. The resulting thick pulp was distributed between a saturated aqueous solution of NH4Cl and Et2O. Drying of the combined organic phases over Na2SO4 and evaporation of the solvent yielded 6.1 g (69%) of N-benzylindoline MS: 210 (MH+).

Workup

  1. customat 0° C.
  2. waitfor 2 hrs at 60° C
  3. dry with materialDrying of the combined organic phases over Na2SO4 and evaporation of the solvent

Sources & evidence

ORD record
ord-b0de48b42cb846af9b29dfbb69570dcc
Source dataset
uspto-grants-2009_02
Patent number
US07485652B2

Reaction notes

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