Thionyl Chloride → HCID 13769172, compound

HRID 2232552Notes

Reaction equation

HRID 2232552 reaction equation
[C:1]1([C:7]2[CH:16]=[C:15]([CH2:17][CH2:18][C:19]([OH:21])=O)[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1>C(Cl)(Cl)Cl.C(OCC)(=O)C>[C:1]1([C:7]2[CH:16]=[C:15]([CH2:17][CH2:18][C:19]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[O:21])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 31268PyrrolidineHCID 21283615HCID 21283615, compound

Product 1

HCID 13769172HCID 13769172, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

The procedure is as in Example 16, starting with 2-phenyl-4-quinolinepropanoic acid (3 g), thionyl chloride (2.3 cc) in chloroform (150 cc) and pyrrolidine (2.7 cc). The residue is stirred for two hours with silica gel (36 g) in ethyl acetate (80 cc). The silica is removed by filtration and washed with ethyl acetate (7×10 cc). The organic phases are combined and concentrated under reduced pressure. After recrystallization of the residue in ethyl acetate, 1-[3-(2-phenyl-4-quinolyl)propionyl]pyrrolidine (2 g), m.p. 116° C., is obtained.

Workup

  1. customThe silica is removed by filtration
  2. washwashed with ethyl acetate (7×10 cc)
  3. concentrationconcentrated under reduced pressure
  4. customAfter recrystallization of the residue in ethyl acetate

Sources & evidence

ORD record
ord-63de4c1919ef40ca82ddd0b7dec277ec
Source dataset
uspto-grants-1988_11
Patent number
US04788204

Reaction notes

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