Pyrrolidine → 8-Bromo-3-pyrrolidino-1,2-dihydronaphthalene

HRID 1683265Notes

Reaction equation

HRID 1683265 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][C:9](=O)[CH2:8][CH2:7]2.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][CH2:9][C:8]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[CH:7]2

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 41361878-Bromo-1,2,3,4-tetrahydronaphthalen-2-one

Product 1

HCID 190432148-Bromo-3-pyrrolidino-1,2-dihydronaphthalene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 8-bromo-2-tetralone (10 gm, 44.4 mMol) in toluene (175 ml) was added pyrrolidine (6.6 ml), and the solution was stirred at reflux for three hours. The volatiles were removed in vacuo to give 8-bromo-3-pyrrolidino-1,2-dihydronaphthalene as a brown oil. To this oil in p-dioxane (60 mL) was added methyl iodide (20 mL, 322 mMol), and the resulting solution was stirred at reflux for eighteen hours. The reaction mixture was diluted with water (60 mL) and acetic acid (3.2 mL), and heating was continued for an additonal three hours. After this time the solution was cooled to room temperature and the volatiles removed in vacuo. The residue was suspended in water and extracted well with diethyl ether. The organic phases were combined, washed with saturated aqueous NaHCO3, dried with Na2SO4 and concentrated in vacuo to give an orange oil. Purification by flash chromatography (33% diethyl ether in hexane) gave the title compound as a light orange oil (6.88 65%).

Workup

  1. temperatureat reflux for three hours
  2. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-26aa68955799422bb3eaf1ea78ebfbc8
Source dataset
uspto-grants-1997_06
Patent number
US05637624

Reaction notes

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