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

HRID 1042720Notes

Reaction equation

HRID 1042720 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-8405293d9fd246498ad6a3197f6c2ecf
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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