Hydrochloric Acid → 2-Fluoro-4-(piperazin-1-YL)benzonitrile

HRID 432598Notes

Reaction equation

HRID 432598 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[C:16]([F:22])[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>CO>[F:22][C:16]1[CH:15]=[C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:19]=[CH:18][C:17]=1[C:20]#[N:21]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54552536Tert-butyl 4-(4-cyano-3-fluorophenyl)piperazine-1-carboxylate

Product 1

HCID 187600452-Fluoro-4-(piperazin-1-YL)benzonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(4-cyano-3-fluoro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (6.97 g, 22.83 mmol) in methanol (250 mL) was saturated with HCl gas and stirred at ambient temperature overnight. The reaction was concentrated, saturated sodium bicarbonate (250 mL) was added and the slurry was stirred for 1 hour. The resulting solid was filtered off, rinsed well with water, air dried then evacuated overnight. As water was removed from the solid, it turned to a milky yellow solid which slowly solidified to give 2-fluoro-4-piperazin-1-yl-benzonitrile as a waxy solid (3.84 g, 82%).

Workup

  1. concentrationThe reaction was concentrated
  2. additionsaturated sodium bicarbonate (250 mL) was added
  3. stirringthe slurry was stirred for 1 hour
  4. filtrationThe resulting solid was filtered off
  5. washrinsed well with water, air
  6. customdried
  7. customthen evacuated overnight
  8. customAs water was removed from the solid, it

Sources & evidence

ORD record
ord-71dbd7e58f2449e983f4a74c2a26a277
Source dataset
uspto-grants-2003_12
Patent number
US06664258B1

Reaction notes

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