Tert-butyl (2-chloro-5-cyano-3-(morpholinomethyl)phenyl)carbamate → 3-Amino-4-chloro-5-(morpholinomethyl)benzonitrile

HRID 921768Notes

Reaction equation

HRID 921768 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:6][C:5]([C:15]#[N:16])=[CH:4][C:3]=1[NH:17]C(=O)OC(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:17][C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([CH2:8][N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[C:2]=1[Cl:1])[C:15]#[N:16]

Participants

4

Reactant 1

HCID 86708657Tert-butyl (2-chloro-5-cyano-3-(morpholinomethyl)phenyl)carbamate

Product 1

HCID 867086563-Amino-4-chloro-5-(morpholinomethyl)benzonitrileYield 99.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl (2-chloro-5-cyano-3-(morpholinomethyl)phenyl)carbamate (45 mg, 0.128 mmol) in a mixture of DCM (2 mL) and TFA (2 mL) was left stirring at room temperature for 1 hr. The solvent was removed and the residue was dissolved in MeOH and applied onto an SCX column. This was washed with MeOH and the product was eluted with 2N NH3 in MeOH. The solvent was removed to leave 3-amino-4-chloro-5-(morpholinomethyl)benzonitrile (32 mg).

Workup

  1. waitwas left
  2. customThe solvent was removed
  3. dissolutionthe residue was dissolved in MeOH
  4. washThis was washed with MeOH
  5. washthe product was eluted with 2N NH3 in MeOH
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-2096d7bd584d461886d529bf5f79f21d
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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