Hydrochloric Acid → (S)-1-(2-nitro-4-(trifluoromethyl)phenyl)piperidin-3-amine dihydrochloride

HRID 502764Notes

Reaction equation

HRID 502764 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[N:14]1[CH2:19][CH2:18][CH2:17][C@H:16]([NH:20]C(=O)OC(C)(C)C)[CH2:15]1)([O-:3])=[O:2].[ClH:28]>>[ClH:28].[ClH:28].[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:7]=[CH:6][C:5]=1[N:14]1[CH2:19][CH2:18][CH2:17][C@H:16]([NH2:20])[CH2:15]1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 16109027(S)-tert-butyl 1-(2-nitro-4-(trifluoromethyl)phenyl)piperidin-3-ylcarbamate

Product 1

HCID 16109043(S)-1-(2-nitro-4-(trifluoromethyl)phenyl)piperidin-3-amine dihydrochloride

Procedure

A solution of (S)-tert-butyl 1-(2-nitro-4-(trifluoromethyl)phenyl)piperidin-3-ylcarbamate (15.64 g, 40 mmol) was cooled to 7° C. and hydrochloric acid 4.0 M dioxane (80 ml, 321 mmol) was added and the mixture allowed to warm to ambient temperature. The orange solution was allowed to stir for 14 h, at which point it was concentrated in vacuo to give (S)-1-(2-nitro-4-(trifluoromethyl)phenyl)piperidin-3-amine dihydrochloride as a yellow solid. MS m/z=290 [M+H]+. Calc'd for C12H14F3N3O2: 289.

Workup

  1. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-124f9a05a12648d5aa30a9a5c71066b3
Source dataset
uspto-grants-2010_08
Patent number
US07776869B2

Reaction notes

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