Hydrochloric Acid → HCID 87158597, compound

HRID 2206909Notes

Reaction equation

C(OC(=O)[NH:7][CH2:8][C:9]1[C:10]([CH3:33])=[N:11][C:12]([N:15]2[CH2:19][CH2:18][C:17]([C:24]3[CH:29]=[C:28]([Cl:30])[C:27]([Cl:31])=[C:26]([Cl:32])[CH:25]=3)([C:20]([F:23])([F:22])[F:21])[CH2:16]2)=[CH:13][CH:14]=1)(C)(C)C.C(O)C.Cl.[OH-].[Na+]>O>[CH3:33][C:10]1[C:9]([CH2:8][NH2:7])=[CH:14][CH:13]=[C:12]([N:15]2[CH2:19][CH2:18][C:17]([C:24]3[CH:25]=[C:26]([Cl:32])[C:27]([Cl:31])=[C:28]([Cl:30])[CH:29]=3)([C:20]([F:22])([F:23])[F:21])[CH2:16]2)[N:11]=1

Participants

Conditions

Temperature: 50 °C

Procedure

t-Butyl({2-methyl-6-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-pyridin-3-yl}methyl)carbamate (0.95 g) was added to ethanol (25 ml) and then to the solution was added conc. hydrochloric acid (5 ml) in small portions at room temperature, and then heated at 50° C. for 3 hours. After cooling the mixture to the room temperature, the reaction mixture was diluted with water (100 ml). The pH was adjusted to 11 by using an aqueous solution of sodium hydroxide and the solution was extracted with ethyl acetate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography to obtain 1-({2-methyl-6-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]pyridin-3-yl}methanamine (0.6 g).

Workup

temperatureAfter cooling the mixture to the room temperature
extractionthe solution was extracted with ethyl acetate
distillationThe solvent was distilled off under reduced pressure
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-b52079cfbded4e19b114422221f7b825
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09375000B2

Reaction notes

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