Triethylamine → HCID 11011278, compound

HRID 1756237Notes

Reaction equation

HRID 1756237 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].C(N(CC)CC)C.[N:18]1([C:23]2[CH2:27][CH2:26][CH2:25][CH:24]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:3]([C:4]([C:24]2[CH2:25][CH2:26][CH2:27][C:23]=2[N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:5])=[CH:7][CH:8]=[CH:9][N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81570Pyrrolidine, 1-(1-cyclopenten-1-yl)-HCID 27745412-Chloronicotinoyl chloride

Product 1

HCID 11011278HCID 11011278, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Dissolve 2-chloronicotinoyl chloride (0.10 mole) in CHCl3 (90 ml). Add the resulting solution to a 5° C. solution of triethylamine (0.10 mole) and an enamine, 1-(1-pyrrolidinyl)-1-cyclopentene (0.10 mole), dissolved in CHCl3 (90 ml). Allow C-acylation to proceed for 21 hrs., while the temperature of the reaction mixture rises to 25° after the second hour. Monitor the course of the reaction by thin-layer chromatography as needed. Wash the resulting solution with water,-aqueous NaHCO3 solution, and with water. After drying, carefully evaporate solvent to obtain the enaminoketone, (2-chloro-3-pyridinyl)[2-(1-pyrrolidinyl)-1-cyclopenten-1-yl]methanone, m.p. 102.5°-104.0° C., after recrystallization from ethyl acetate. This compound is referred to in Examples 1 and 3 below as Compound 1.

Workup

  1. customrises to 25°
  2. customMonitor the course of the reaction by thin-layer chromatography
  3. washWash the resulting solution with water,-aqueous NaHCO3 solution
  4. customAfter drying

Sources & evidence

ORD record
ord-5f2f281314164c5e8707d429c0303644
Source dataset
uspto-grants-1995_08
Patent number
US05439916

Reaction notes

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