Trifluoroacetic acid → 5-chloro-2-(aminocarbonylmethyloxy)benzylamine

HRID 1169884Notes

Reaction equation

HRID 1169884 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[O:16][CH2:17][C:18](=[O:20])[NH2:19])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:15][C:13]1[CH:12]=[CH:11][C:10]([O:16][CH2:17][C:18]([NH2:19])=[O:20])=[C:9]([CH:14]=1)[CH2:8][NH2:7]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11370462HCID 11370462, compound

Product 1

HCID 111834945-chloro-2-(aminocarbonylmethyloxy)benzylamineYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 79 (200 mg, 0.63 mmol) was treated with a solution at 15% of TFA in CH2Cl2 at room temperature for 45 min. The solution was concentrated in vacuo and water (10 mL) was added. The aqueous phase was washed with Et2O, basified with aqueous 2N NaOH, and extracted with CHCl3 (10 mL×3) obtaining 130 mg of a white solid (80) (yield 96%). 1H NMR (CDCl3, 300 MHz) δ8.37 (br s, 1H), 7.29-7.22 (m, 2H), 6.82 (d, J=9.3 Hz, 1H), 5.44 (br s, 1H), 3.8(s, 2H), 3.89 (s, 2H). MS (m/e) (API-ES) 215 (M+H)+, m.p. 135-137° C.

Workup

  1. concentrationThe solution was concentrated in vacuo and water (10 mL)
  2. additionwas added
  3. washThe aqueous phase was washed with Et2O
  4. extractionextracted with CHCl3 (10 mL×3)

Sources & evidence

ORD record
ord-e41f96952aa146f3a6f2954fbd47e1f3
Source dataset
uspto-grants-2010_11
Patent number
US07825126B2

Reaction notes

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