Benzylamine → 2,3-Dihydro-4-methoxy-2-(phenylmethyl)-1H-isoindole

HRID 1494832Notes

Reaction equation

HRID 1494832 reaction equation
Br[CH2:2][C:3]1[C:8]([CH2:9]Br)=[CH:7][CH:6]=[CH:5][C:4]=1[O:11][CH3:12].[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.[OH-].[Na+].C1(C)C=CC=CC=1>[CH2:13]([N:20]1[CH2:2][C:3]2[C:8](=[CH:7][CH:6]=[CH:5][C:4]=2[O:11][CH3:12])[CH2:9]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 2

HCID 7504BenzylamineHCID 11277819HCID 11277819, compound

Product 1

HCID 151678902,3-Dihydro-4-methoxy-2-(phenylmethyl)-1H-isoindole

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolventHCID 14798Sodium HydroxideSolvent

Procedure

The 2,3-bis-(bromomethyl)anisole prepared above and 1.5 g of benzyltriethylammonium chloride were dissolved in a mixture of 80 ml of aqueous 50% sodium hydroxide and 350 ml of toluene. To the solution was dropwise added 21.6 g of benzylamine over 15 minutes while stirring at room temperature. After stirring for one day for one day, the organic layer was separated and washed with brine. After concentration, the residue was purified by chromatography on silica gel (benzene/ethyl acetate=15/1) to give 15.2 g of 2-benzyl-4-methoxyisoindoline as an oily substance.

Workup

  1. customover 15 minutes
  2. stirringAfter stirring for one day for one day
  3. customthe organic layer was separated
  4. washwashed with brine
  5. concentrationAfter concentration
  6. customthe residue was purified by chromatography on silica gel (benzene/ethyl acetate=15/1)

Sources & evidence

ORD record
ord-6e61a049ef314c68995752e7f8bab213
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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