Hydrogen Bromide → 1-[(1H-Pyrrol-2-yl)methylidene]pyrrolidin-1-ium bromide

HRID 2071691Notes

Reaction equation

HRID 2071691 reaction equation
[BrH:1].[NH:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1.[NH:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH:12]=O.Br.N1CCCC1>C(Cl)(Cl)Cl>[Br-:1].[NH:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH:12]=[N+:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 13854Pyrrole-2-carboxaldehydeHCID 31268PyrrolidineHCID 18621471Pyrrolidine--hydrogen bromide (1/1)

Product 1

HCID 214118841-[(1H-Pyrrol-2-yl)methylidene]pyrrolidin-1-ium bromide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 81.0 g (1.00 mole) of hydrogen bromide in 1000 ml of absolute chloroform is added dropwise with cooling and stirring a solution of 80.0 g (1.12 mole) of pyrrolidine in 100 ml of absolute chloroform. Then 95.1 g (1.00 mole) of pyrrole-2-carboxaldehyde is added to the above pyrrolidine hydrobromide solution along with 1 pound of Linde Molecular sieve 5A. The reaction mixture is stirred at ambient temperature for 3 hours, then is filtered through filter aid, washing well with chloroform. The combined filtrate and washings are evaporated in vacuo and the residue is recrystallized twice from acetonitrile to give 1-(pyrrol-2-ylmethylene)pyrrolidinium bromide; m.p. 113°-116° C.

Workup

  1. temperaturewith cooling
  2. filtrationis filtered
  3. filtrationthrough filter aid
  4. washwashing well with chloroform
  5. customThe combined filtrate and washings are evaporated in vacuo
  6. customthe residue is recrystallized twice from acetonitrile

Sources & evidence

ORD record
ord-3162f48fa66f4d33bf3d44dfc2dae8d9
Source dataset
uspto-grants-1977_09
Patent number
US04048191

Reaction notes

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