Hydrochloric Acid → (S)-4-(3-methylpiperazin-1-yl)benzonitrile hydrochloride

HRID 69689Notes

Reaction equation

HRID 69689 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[C@@H:11]([CH3:22])[CH2:10]2)=[CH:5][CH:4]=1)#[N:2].[ClH:23]>O1CCOCC1.C(OCC)C>[ClH:23].[CH3:22][C@@H:11]1[NH:12][CH2:13][CH2:14][N:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH2:10]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58324511(S)-tert-butyl 4-(4-cyanophenyl)-2-methylpiperazine-1-carboxylate

Product 1

HCID 66775307(S)-4-(3-methylpiperazin-1-yl)benzonitrile hydrochlorideYield 94%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

(S)-tert-butyl 4-(4-cyanophenyl)-2-methylpiperazine-1-carboxylate (0.404 g, 1.340 mmol) was diluted with 4.0M HCl in dioxane (3 mL) and stirred for 30 min. The thick white precipitate that formed was diluted with ethyl ether (10 mL) and stirred until a fine suspension resulted. The precipitate was filtered under nitrogen and dried in vacuum to afford a white solid (300 mg, 94%). [M+H] calc'd for C12H15N3, 201; found, 201.

Workup

  1. customThe thick white precipitate that formed
  2. stirringstirred until a fine suspension
  3. customresulted
  4. filtrationThe precipitate was filtered under nitrogen
  5. customdried in vacuum

Sources & evidence

ORD record
ord-9ed9003808344a199bf693b99464c7e9
Source dataset
uspto-grants-2014_09
Patent number
US08822470B2

Reaction notes

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