Trifluoroacetic acid → N-{1-[2-(aminomethyl)-4-chlorobenzyl]-2,2,2-trifluoroethyl}-N-(4-methoxyphenyl)amine

HRID 1058251Notes

Reaction equation

HRID 1058251 reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:24][CH:25]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)[C:26]([F:29])([F:28])[F:27])=[C:13]([CH:23]=1)[CH2:14][NH:15]C(=O)OC(C)(C)C>C(Cl)Cl>[NH2:15][CH2:14][C:13]1[CH:23]=[C:9]([Cl:8])[CH:10]=[CH:11][C:12]=1[CH2:24][CH:25]([NH:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)[C:26]([F:29])([F:28])[F:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18672399Tert-butyl 5-chloro-2-{2-[(4-methoxyphenyl)amino]-3,3,3-trifluoropropyl}benzylcarbamate

Product 1

HCID 18672307N-{1-[2-(aminomethyl)-4-chlorobenzyl]-2,2,2-trifluoroethyl}-N-(4-methoxyphenyl)amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL) was added to a stirred solution of tert-butyl 5-chloro-2-{2-[(4-methoxyphenyl)amino]-3,3,3-trifluoropropyl}benzylcarbamate (0.205 g, 0.447 mmol) in CH2Cl2 (2 mL). After 1 h the solvent was evaporated in vacuo and the residue was partitioned between EtOAc and saturated aqueous Na2CO3. The organic layer was dried (Na2SO4) and evaporated in vacuo to give N-{1-[2-(aminomethyl)-4-chlorobenzyl]-2,2,2-trifluoroethyl}-N-(4-methoxyphenyl)amine (0.182 a solid; 1H NMR (CDCl3, 400 MHz) δ 3.02 (dd, J=10.9 and 14.2 Hz, 1H), 3.11 (dd, J=3.4 and 14.2 Hz, 1H), 3.69 (s, 3H), 3.86 (d, J=12.9 Hz, 1H), 3.97 (d, J=12.9 Hz, 1H), 3.98 (obscured m, 1H), 6.44 (d, J=8.8 Hz, 2H), 6.66 (d, J=8.8 Hz, 2H), 7.19 (s, 2H), 7.22 (s, 1H).

Workup

  1. customAfter 1 h the solvent was evaporated in vacuo
  2. customthe residue was partitioned between EtOAc and saturated aqueous Na2CO3
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-162dba6507e44b2f8d2ad2c27b99e3fa
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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