1,4-Dibromobutane → 1-(3-methoxyphenyl)pyrrolidine

HRID 902705Notes

Reaction equation

HRID 902705 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:9])[CH:6]=[CH:7][CH:8]=1.Br[CH2:11][CH2:12][CH2:13][CH2:14]Br.C(N(C(C)C)CC)(C)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 108243-MethoxyanilineHCID 81531Diisopropylethylamine

Product 1

HCID 112175611-(3-methoxyphenyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirring solution of 3-methoxy-phenylamine (571 mg, 4.6 mmol) in anhydrous toluene (40 ml) was added 1,4-dibromo-butane (1.0 g, 4.6 mmol) and diisopropylethylamine (0.59 g, 4.6 mmol). The resulting solution was heated to reflux for 24 hours and then concentrated in vacuo. The crude material was purified by column chromatography over silica gel (silica gel 60, EM science, 5% EtOAc:hexanes) and the title compound was obtained as an oil (754 mg, 92%). MS(ES) m/e 178.4 ([M+H]+).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 24 hours
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by column chromatography over silica gel (silica gel 60, EM science, 5% EtOAc:hexanes)

Sources & evidence

ORD record
ord-20689b8aeeea45e7a08ff27b93a3093a
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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