Pyrrolidine → HCID 10362856, compound

HRID 2380339Notes

Reaction equation

HRID 2380339 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:9]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](O)=[O:24])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1>O1CCCC1>[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:9]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([N:38]3[CH2:42][CH2:41][CH2:40][CH2:39]3)=[O:24])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 682631,1'-CarbonyldiimidazoleHCID 100198536-[(4-Phenyl-2-quinolyl)oxy]hexanoic acid

Product 1

HCID 10362856HCID 10362856, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5 g of 6-[(4-phenyl-2-quinolyl)oxy]hexanoic acid in 120 cc of tetrahydrofuran is added 2.9 g of 1,1'-carbonyldiimidazole. The mixture is stirred for 2 hours to 50° C. After cooling, 1.3 g of pyrrolidine is added and the mixture is stirred at room temperature overnight. The tetrahydrofuran is removed in vacuo and the residue partitioned between ethyl acetate and water. The ethyl acetate solution is washed with water, dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue is then purified by flash chromatography on silica gel (30-60mm; eluent: 3:7 cyclohexane/ethyl acetate) to give 1-[6-(4-phenyl-2-quinolyloxy)hexanoyl]pyrrolidine as a white solid m.p.=52°-54° C.)

Workup

  1. temperatureAfter cooling
  2. stirringthe mixture is stirred at room temperature overnight
  3. customThe tetrahydrofuran is removed in vacuo
  4. customthe residue partitioned between ethyl acetate and water
  5. washThe ethyl acetate solution is washed with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resultant residue is then purified by flash chromatography on silica gel (30-60mm; eluent: 3:7 cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-b3e1525099984d1ebedba9a675f5be3f
Source dataset
uspto-grants-1994_11
Patent number
US05366982

Reaction notes

Loading…