1,4-Dibromobutane → HCID 13083323, compound

HRID 325868Notes

Reaction equation

HRID 325868 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:12][CH2:13][NH2:14])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Br[CH2:16][CH2:17][CH2:18][CH2:19]Br.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:12][CH2:13][N:14]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 10340Sodium CarbonateHCID 13083312HCID 13083312, compound

Product 1

HCID 13083323HCID 13083323, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2-[1-(4-Chlorophenyl)cyclobutyl]ethylamine (12 g) prepared as described in Example 1, 1,4-dibromobutane (12.4 g) and anhydrous sodium carbonate (14.3 g) were mixed in xylene (100 ml) and the mixture heated under reflux with stirring for sixteen hours. The mixture was cooled, filtered and the xylene removed by evaporation to give a residue which on distillation gave N-2-[1-(4-chlorophenyl)cyclobutyl]ethylpyrrolidine (b.p. 148°-150°/1.5 mm Hg) (Formula 1 R1,R2 =H; R3 and R4 together with the nitrogen atom forming a pyrrolidine ring; R5 =4-Cl; R6, R7 and R8 =H).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. customthe xylene removed by evaporation
  6. customto give a residue which
  7. distillationon distillation

Sources & evidence

ORD record
ord-98f71ca1081a45afbbc179166c41f5bf
Source dataset
uspto-grants-1984_04
Patent number
US04443449

Reaction notes

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