HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 379674
Notes
Print preview

Reaction equation

HRID 379674 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([OH:13])=O)=[CH:5][CH:4]=1)#[N:2].CN1CCOCC1.ClC(OCC(C)C)=O.[F:29][C:30]([F:45])([F:44])[C:31]([NH:33][C:34]1[CH:35]=[C:36]2[C:41](=[CH:42][CH:43]=1)[NH:40][CH2:39][CH2:38][CH2:37]2)=[O:32]>O1CCCC1.C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][C:11]([N:40]2[C:41]3[C:36](=[CH:35][C:34]([NH:33][C:31](=[O:32])[C:30]([F:44])([F:45])[F:29])=[CH:43][CH:42]=3)[CH2:37][CH2:38][CH2:39]2)=[O:13])=[CH:7][CH:8]=1)#[N:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 93617423-(4-Cyanophenyl)-propionic acidHCID 10421907N-(1,2,3,4-tetrahydro-6-quinolyl)trifluoroacetamide

Product 1

HCID 154107711-[3-(4-Cyano-phenyl)propionyl]-6-trifluoroacetylamino-1,2,3,4-tetrahydro-quinoline

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
2×
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-20 °C

Procedure

10 g (0.057 mol) of 3-(4-cyano-phenyl)propionic acid and 6.6 g (0.065 mol) of N-methyl-morpholine are dissolved in 250 ml tetrahydrofuran and cooled to −20° C. Then 8.2 g (0.06 mol) of isobutyl chloroformate are added dropwise. 13.9 g (0.057 mol) of 6-(trifluoroacetylamino)-1,2,3,4-tetrahydro-quinoline in 200 ml tetrahydrofuran are then added and the solution is left to heat up to ambient temperature overnight. It is then diluted with 200 ml of ethyl acetate and washed with 2×80 ml of 0.5 N hydrochloric acid and then 100 ml of sodium hydrogen carbonate solution. The organic phase is dried over sodium sulphate and concentrated by evaporation in vacuo.

Workup

  1. waitthe solution is left
  2. temperatureto heat up to ambient temperature overnight
  3. washwashed with 2×80 ml of 0.5 N hydrochloric acid
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. concentrationconcentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-bd685e2218f54e7ebfdb5b8910993818
Source dataset
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06300342B1

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes