1,4-Dibromobutane → 3-(2-Pyrrolidin-1-ylethyl)anisole

HRID 35600

Reaction equation

HRID 35600 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][NH2:17])[CH:12]=[CH:13][CH:14]=1.Br[CH2:19][CH2:20][CH2:21][CH2:22]Br>C1(C)C(C)=CC=CC=1>[N:17]1([CH2:16][CH2:15][C:11]2[CH:10]=[C:9]([O:8][CH3:7])[CH:14]=[CH:13][CH:12]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 10340Sodium CarbonateHCID 748663-Methoxyphenethylamine

Product 1

HCID 183650073-(2-Pyrrolidin-1-ylethyl)anisole

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A stirred suspension of anhydrous sodium carbonate (0.923 g), 2-(3-methoxyphenyl)ethylamine (0.5 g) and 1,4-dibromobutane (0.43 ml) in dry xylene (5.5 ml) was heated under reflux for 16 hours. The reaction mixture was allowed to cool to room temperature and was filtered. The filtrate was extracted with 5N hydrochloric acid. The acidic extracts were washed with ether and then basified with 5N sodium hydroxide solution and extracted with ether. The ether extracts were washed with water, dried and the ether removed by evaporation to give 3-(2-pyrrolidin-1-ylethyl)anisole.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. filtrationwas filtered
  4. extractionThe filtrate was extracted with 5N hydrochloric acid
  5. washThe acidic extracts were washed with ether
  6. extractionextracted with ether
  7. washThe ether extracts were washed with water
  8. customdried
  9. customthe ether removed by evaporation

Sources & evidence

ORD record
ord-dc7075a1af0549cfa7884368ccc5eb71
Source dataset
uspto-grants-1988_08
Patent number
US04767769

Linked notes

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