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

HRID 1644991Notes

Reaction equation

HRID 1644991 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-a5120807d0de4145a20d57a8ba986135
Source dataset
uspto-grants-2012_02
Patent number
US08124606B2

Reaction notes

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