Pyrrolidine → 1-{2-[(6-bromo-2-naphthyl)oxy]ethyl}pyrrolidine

HRID 860857Notes

Reaction equation

HRID 860857 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH2:13][CH2:14]Br)[CH:8]=2)[CH:3]=1.[NH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][CH2:13][CH2:14][N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)[CH:6]=[CH:5]2

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 22131449HCID 22131449, compound

Product 1

HCID 100416631-{2-[(6-bromo-2-naphthyl)oxy]ethyl}pyrrolidineYield 98%

Conditions

Temperature
80 °C

Procedure

In a flask containing 0.5 g (1.5 mmol) the product from Example 37A, 10 mL of pyrrolidine was added. After stirring at 80° C. for 3 h, the reaction mixture was concentrated under vacuum. The residue was diluted with 100 mL of CH2Cl2 and washed sequentially with water, sodium bicarbonate and brine, dried and evaporated under reduced pressure. Silica gel chromatography (MeOH:CH2Cl2, 95:5) gave the desired material in 98% yield. 1HNMR (300 MHz, CDCl3) δ 1.80 (m, 4H), 2.6 (m, 4H), 2.97 (t, 2H), 4.20 (t, 2H), 2.49 (m, 2H) 7.10–7.90 (m, 6H); MS (ESI) m/z 321 (M+H)+.

Workup

  1. additionwas added
  2. concentrationthe reaction mixture was concentrated under vacuum
  3. additionThe residue was diluted with 100 mL of CH2Cl2
  4. washwashed sequentially with water, sodium bicarbonate and brine
  5. customdried
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e031b4aa4d5f404685c5df94b1e979e2
Source dataset
uspto-grants-2006_12
Patent number
US07153889B2

Reaction notes

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