4-Methylmorpholine → 1-[3-(4-Cyano-phenyl)propionyl]-6-phenylsulphonamido-1,2,3,4-tetrahydro-quinoline

HRID 379679Notes

Reaction equation

HRID 379679 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:13])C(O)=O)=[CH:5][CH:4]=1)#[N:2].CN1CC[O:18][CH2:17]C1.ClC(OCC(C)C)=O.[C:29]1([S:35]([NH:38][C:39]2[CH:40]=[C:41]3[C:46](=[CH:47][CH:48]=2)[NH:45][CH2:44][CH2:43][CH2:42]3)(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O1CCCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:13][C:17]([N:45]2[C:46]3[C:41](=[CH:40][C:39]([NH:38][S:35]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)(=[O:37])=[O:36])=[CH:48][CH:47]=3)[CH2:42][CH2:43][CH2:44]2)=[O:18])=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 110335346-Phenylsulphonamido-1,2,3,4-tetrahydro-quinolineHCID 225698632-(4-Cyanophenyl)propanoic acid

Product 1

HCID 111023311-[3-(4-Cyano-phenyl)propionyl]-6-phenylsulphonamido-1,2,3,4-tetrahydro-quinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-35 °C

Procedure

4.6 g 3-(4-cyano-phenylpropionic acid are dissolved with 2.8 g of N-methyl-morpholine in 120 ml of tetrahydrofuran and cooled to −35° C. To this solution are added 3.6 ml of isobutyl chloroformate, stirring is continued for half an hour and then at −40° C. 7.2 g of 6-phenylsulphonamido-1,2,3,4-tetrahydro-quinoline are added (see Example IV). After 2 hours the solution is slowly allowed to come back to ambient temperature and stirring is continued overnight. Then it is concentrated by evaporation and the residue is taken up in ethyl acetate and water. The organic phase is again washed with water, dried and concentrated by evaporation. The oil remaining is chromatographed over a silica gel column with ethyl acetate/petroleum ether (7:3).

Workup

  1. waitis continued for half an hour
  2. customat −40° C
  3. customto come back to ambient temperature
  4. stirringstirring
  5. waitis continued overnight
  6. concentrationThen it is concentrated by evaporation
  7. washThe organic phase is again washed with water
  8. customdried
  9. concentrationconcentrated by evaporation
  10. customThe oil remaining is chromatographed over a silica gel column with ethyl acetate/petroleum ether (7:3)

Sources & evidence

ORD record
ord-0b39e586aeb84bb09fdd97e72d4a11f4
Source dataset
uspto-grants-2001_10
Patent number
US06300342B1

Reaction notes

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