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

HRID 1430949Notes

Reaction equation

HRID 1430949 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 100%

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 RT 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, 100% yield).

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-0141db0a044b48d88270cbc4c60b91fd
Source dataset
uspto-grants-2015_01
Patent number
US08940736B2

Reaction notes

Loading…