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

HRID 379674Notes

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]

Participants

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

waitthe solution is left
temperatureto heat up to ambient temperature overnight
washwashed with 2×80 ml of 0.5 N hydrochloric acid
dry with materialThe organic phase is dried over sodium sulphate
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

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