Ammonia → HCID 86708474, compound

HRID 921624Notes

Reaction equation

HRID 921624 reaction equation
C(OC([NH:8][C:9]1[C:10]([Cl:30])=[C:11]([N:17]2[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]2)[CH:12]=[C:13]([C:15]#[N:16])[CH:14]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.N>ClCCl>[NH2:8][C:9]1[CH:14]=[C:13]([CH:12]=[C:11]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[C:10]=1[Cl:30])[C:15]#[N:16]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 86708475HCID 86708475, compound

Product 1

HCID 86708474HCID 86708474, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(I11B): To the stirred solution of tert-butyl 4-(3-((tert-butoxycarbonyl)amino)-2-chloro-5-cyanophenyl)piperazine-1-carboxylate (2.0 g, 4.58 mmol) in dichloromethane (40 mL) was added trifluoroacetic acid (8.89 mL, 115 mmol) slowly drop wise at room temperature, stirred it for 3 hours at room temperature. On completion of the reaction, the reaction mixture was diluted with methylene chloride (300 mL), cooled it to 0° C., basified with ammonia solution and extracted twice, the organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The crude material was washed with diethyl ether several times and dried under vacuum to get 3-amino-4-chloro-5-(piperazin-1-yl)benzonitrile (1.0 g) as a brown color solid.

Workup

  1. customslowly drop wise at room temperature
  2. customOn completion of the reaction
  3. temperaturecooled it to 0° C.
  4. extractionextracted twice
  5. washthe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. washThe crude material was washed with diethyl ether several times
  9. customdried under vacuum

Sources & evidence

ORD record
ord-a1f31e999a6b4183a40fac12bee4b4f3
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

Loading…