3-Bromocyclohexene → HCID 67304537, compound

HRID 533364Notes

Reaction equation

HRID 533364 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].Br[CH:14]1[CH2:19][CH2:18][CH2:17][CH:16]=[CH:15]1>CN(C=O)C>[CH:18]1([N:5]2[C:1](=[O:11])[C:2]3[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4]2=[O:6])[CH2:17][CH2:16][CH:15]=[CH:14][CH2:19]1

Participants

4

Reactant 2

HCID 1370573-BromocyclohexeneHCID 24194345Phthalimide potassium salt

Product 1

HCID 67304537HCID 67304537, compoundYield 234.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of potassium phthalimide (1.85 g, 3 mmol) and 3-bromocyclohexene (1.79 g, 3 mmol) in DMF (15 mL) was stirred in a 100° C. oil bath for 12 h. The cooled reaction mixture was poured into ice water. The solid was collected by filtration and purified by flash chromatography with CH2Cl2 as the eluent to afford compound 221 (1.6 g, 72%) as pink crystals; mp 114° C.; 1H NMR (CDCl3) δ 7.73-7.69 (m, 2H), 7.62-7.58 (m, 2H), 5.85-5.82 (m, 1H), 5.47-5.44 (m, 1H), 4.80-4.78 (m, 1H), 2.14-2.00 (m, 3H), 1.86-1.78 (m, 2H), 1.64-1.58 (m, 1H).

Workup

  1. customThe cooled reaction mixture
  2. filtrationThe solid was collected by filtration
  3. custompurified by flash chromatography with CH2Cl2 as the eluent

Sources & evidence

ORD record
ord-4724afb22e5a4e3bb66120fb85371024
Source dataset
uspto-grants-2014_10
Patent number
US08853253B2

Reaction notes

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