1,4-Dibromobutane → 1-(4-Bromophenethyl)pyrrolidine

HRID 1916580Notes

Reaction equation

HRID 1916580 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5]Br.Cl.[Br:8][C:9]1[CH:17]=[CH:16][C:12]([CH2:13][CH2:14][NH2:15])=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.O>[Br:8][C:9]1[CH:17]=[CH:16][C:12]([CH2:13][CH2:14][N:15]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 197039732-(4-Bromophenyl)ethan-1-amine--hydrogen chloride (1/1)

Product 1

HCID 121778101-(4-Bromophenethyl)pyrrolidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
75 °C

Procedure

0.51 mL (4.23 mmol) 1,4-dibromobutane in 20 mL acetonitrile is added slowly to a solution of 1.0 g (4.23 mmol) 4-bromo-phenethylamine hydrochloride, 1.8 g (13.0 mmol) K2CO3 and 200 mg (1.20 mmol) Kl in 100 mL acetonitrile at 75° C. and the reaction mixture is stirred for a further 4 h at 75° C. The reaction solution is diluted with 100 mL water and the aqueous phase is extracted with 100 mL EtOAc. The combined organic extracts are washed with saturated NaCl solution, the organic phase is dried over Na2SO4 and the solvent is eliminated i.vac. Further purification is carried out by column chromatography on silica gel (EtOAc/MeOH/NH3 9:1:0.1)

Workup

  1. extractionthe aqueous phase is extracted with 100 mL EtOAc
  2. washThe combined organic extracts are washed with saturated NaCl solution
  3. dry with materialthe organic phase is dried over Na2SO4
  4. customFurther purification

Sources & evidence

ORD record
ord-488fc83eb3934255bdcf9f36d0e594e6
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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