Hydrochloric Acid → 4-[(1S,4S)-2,5-Diazabicyclo[2.2.1]heptan-5-yl]quinoline hydrochloride

HRID 333942Notes

Reaction equation

HRID 333942 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([N:11]2[CH2:16][C@@H:15]3[CH2:17][C@H:12]2[CH2:13][N:14]3C(OC(C)(C)C)=O)=[CH:3][CH:2]=1.[ClH:25]>O1CCOCC1>[ClH:25].[C@H:15]12[CH2:17][C@H:12]([N:11]([C:4]3[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=[CH:2][CH:3]=3)[CH2:16]1)[CH2:13][NH:14]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86691594tert-Butyl (1S,4S)-5-(4-quinolyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Product 1

HCID 668355714-[(1S,4S)-2,5-Diazabicyclo[2.2.1]heptan-5-yl]quinoline hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl (1S,4S)-5-(4-quinolyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (325 mg from step A) was dissolved in a 4M solution of HCl in anhydrous dioxane (4 ml) and stirred for one hour at room temperature. The volatiles were evaporated under reduced pressure, the residue was triturated two times with diethylether and the supernatant removed. The residue was dried in vacuo to obtain 317 mg of a solid. MS (APCI) m/z=225.9 [M+H]+.

Workup

  1. customThe volatiles were evaporated under reduced pressure
  2. customthe residue was triturated two times with diethylether
  3. customThe residue was dried in vacuo

Sources & evidence

ORD record
ord-60e96f84bf0f4e4aa2c21824645165de
Source dataset
uspto-grants-2014_11
Patent number
US08883791B2

Reaction notes

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