Hydrochloric Acid → cis-1-Acetyl-4-[(2-fluorophenyl)amino]-2-methyl-1,2,3,4-tetrahydroquinoline

HRID 2167240Notes

Reaction equation

[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[N:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[CH2:6][CH:5]1[CH3:22])(=[O:3])[CH3:2].C([BH3-])#N.[Na+].Cl.C(=O)([O-])O.[Na+]>CO>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C@H:7]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[CH2:6][C@@H:5]1[CH3:22])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

[Step 2] 60 mg of 1-acetyl-2-methyl-4-[(2-fluorophenyl)imino]-1,2,3,4-tetrahy droquinoline and 28 mg of sodium cyanoborohydride were dissolved in 2 mL of methanol, and the solution was stirred for 18 hours at 50° C. After completion of the reaction, 1 N hydrochloric acid was added to the reaction liquid, and the mixture was stirred for 30 minutes. The reaction liquid was neutralized with a saturated aqueous solution of sodium hydrogen carbonate, and then was extracted with chloroform. The organic layer was washed with a saturated solution of sodium hydrogen carbonate and saturated brine, dehydrated over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by using silica gel chromatography (diethyl ether:hexane=2:1), and thus 53 mg (88%) of the title compound was obtained as a colorless oily substance.

Workup

additionwas added to the reaction liquid
stirringthe mixture was stirred for 30 minutes
customThe reaction liquid
extractionwas extracted with chloroform
washThe organic layer was washed with a saturated solution of sodium hydrogen carbonate and saturated brine
concentrationconcentrated under reduced pressure
customThe resulting residue was purified

Sources & evidence

ORD record: ord-4de06b1383524b0abfcdf44bf42290a3
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045423B2

Reaction notes

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