Pyridine → HCID 3402305, compound

HRID 1706600Notes

Reaction equation

HRID 1706600 reaction equation
[O:1]([C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](Cl)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.N1C=CC=CC=1>O>[O:1]([C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31268PyrrolidineHCID 110753032-Phenoxybenzoyl chloride

Product 1

HCID 3402305HCID 3402305, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7.7 parts of 2-phenoxybenzoyl chloride was added dropwise to a solution of 2.5 parts of pyrrolidine in 20 parts of pyridine at 0°. When the addition was complete the mixture was stirred for 5 hours. The temperature was then allowed to rise to room temperature and the reaction mixture was poured into 100 parts of water. The aqueous solution was then extracted with chloroform, and washed with water. The chloroform layer was dried over magnesium sulfate, removal of the magnesium sulfate by filtration and concentration of the filtrate gave 6.4 parts of N-(2-phenoxybenzoyl)pyrrolidine, NMR (CDCl3) 1.8δ(m,4H,CH2), 3.4δ(m,4H-N-CH2), 7.1δ(m,9H,Aromatic H). The following compounds can be prepared from the 2-substituted benzoyl chloride and the appropriate secondary amine as described above.

Workup

  1. additionWhen the addition
  2. customto rise to room temperature
  3. extractionThe aqueous solution was then extracted with chloroform
  4. washwashed with water
  5. dry with materialThe chloroform layer was dried over magnesium sulfate, removal of the magnesium sulfate by filtration and concentration of the filtrate

Sources & evidence

ORD record
ord-02e3141ad9d74baead51f93f9cf6ccb0
Source dataset
uspto-grants-1980_06
Patent number
US04208205

Reaction notes

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