Benzyl Bromide → 3-[3-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)propyl]-1-(phenylmethyl)pyridinium bromide

HRID 374458Notes

Reaction equation

HRID 374458 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])[CH:2]=1.[CH2:21]([Br:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CC(O)C>[Br-:28].[O:20]=[C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18](=[O:19])[N:10]1[CH2:9][CH2:8][CH2:7][C:3]1[CH:2]=[N+:1]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 135575522-[3-(Pyridin-3-yl)propyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 189971253-[3-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)propyl]-1-(phenylmethyl)pyridinium bromideYield 70.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 2.00 g (7.5 moles) of 2-[3-(3-pyridinyl) propyl]-1H-isoindole-1,3 (2H) -dione, 8 mL of 2-propanol, and 1.71 g (10 mmoles) of benzyl bromide was heated under reflux for 1 hour. The solution was cooled to 0°, and the precipitated product was collected by suction filtration, washed with cold ethyl ether, and dried to afford 3.08 g of 3-[3-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)propyl]-1-(phenylmethyl)pyridinium bromide.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. temperatureThe solution was cooled to 0°
  4. filtrationthe precipitated product was collected by suction filtration
  5. washwashed with cold ethyl ether
  6. customdried

Sources & evidence

ORD record
ord-b50cf8db69624eb288cf5a4a07697aee
Source dataset
uspto-grants-1996_01
Patent number
US05480892

Reaction notes

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