Hydrochloric Acid → {3-(3-Chloro-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}(morpholin-4-yl)methanone

HRID 661208Notes

Reaction equation

N([O-])=O.[Na+].N[C:6]1[N:10]=[C:9]([CH:11]2[CH2:16][CH:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)[CH2:14][N:13]([C:27]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[O:28])[CH2:12]2)[O:8][N:7]=1.[ClH:35]>O>[Cl:35][C:6]1[N:10]=[C:9]([CH:11]2[CH2:16][CH:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)[CH2:14][N:13]([C:27]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[O:28])[CH2:12]2)[O:8][N:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2.59 g (37.6 mmol) of sodium nitrite in 10 ml of water was added dropwise at 0° C. to a solution of 8.00 g (18.8 mmol) of the amine from Example 22A in 200 ml of concentrated hydrogen chloride solution. After the addition had ended, the mixture was stirred at 0° C. for 1 h and then at RT for 2 h. The reaction mixture was diluted with 1 N aqueous hydrogen chloride solution and extracted with dichloromethane. The organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by means of preparative HPLC. Yield: 5.83 g (70% of theory)

Workup

additionAfter the addition
waitat RT for 2 h
extractionextracted with dichloromethane
dry with materialThe organic phase was dried over magnesium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude product was purified by means of preparative HPLC

Sources & evidence

ORD record: ord-12c695903f744bfab3e987d8a1702a9e
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084469B2

Reaction notes

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