Sodium Hydroxide → 4-Pyrrolidinopyridine

HRID 622822Notes

Reaction equation

HRID 622822 reaction equation
[Cl-].C(CC[N+:7]1[CH:12]=[CH:11][C:10](C#N)=[CH:9][CH:8]=1)(=O)N.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.[OH-].[Na+].[OH-].[Na+]>O>[N:15]1([C:10]2[CH:9]=[CH:8][N:7]=[CH:12][CH:11]=2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 159190721-(3-Amino-3-oxopropyl)-4-cyanopyridin-1-ium chlorideHCID 21292233Pyrrolidine sodium hydroxide

Product 1

HCID 755674-Pyrrolidinopyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1-(2-carbamoylethyl)-4-cyanopyridinium chloride (21.2 g; 0.1 mole) dissolved in 15 ml of deionized water was prepared and charged to the dropping funnel. This solution was then added to the pyrrolidine/sodium hydroxide solution at a rate which permitted maintenance of the reaction temperature with stirring at below 5° C. It was held there for an additional hour, after which 14 g (0.175 mole) of a 50% (w/w) sodium hydroxide solution was added dropwise with continued maintenance of the reaction temperature below 5° C. (approximately 45 minutes). The mixture was then heated to reflux and maintained for two hours and then allowed to cool.

Workup

  1. customwas prepared
  2. additioncharged to the dropping funnel
  3. waitIt was held there for an additional hour
  4. temperatureThe mixture was then heated
  5. temperatureto reflux
  6. temperaturemaintained for two hours
  7. temperatureto cool

Sources & evidence

ORD record
ord-0a8c4191d8a54cdcb4bb61c458dedfe6
Source dataset
uspto-grants-1988_09
Patent number
US04772713

Reaction notes

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