Trifluoroacetic acid → 3-(Aminomethyl)-N-(3,5-dichlorobenzyl)-N-(4-fluorobenzyl)benzamide

HRID 1889660Notes

Reaction equation

HRID 1889660 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:32]=[C:33]([Cl:35])[CH:34]=1)[CH2:5][N:6]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)[C:7]([C:9]1[CH:10]=[C:11]([CH:21]=[CH:22][CH:23]=1)[CH2:12][NH:13]C(=O)OC(C)(C)C)=[O:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:13][CH2:12][C:11]1[CH:10]=[C:9]([CH:23]=[CH:22][CH:21]=1)[C:7]([N:6]([CH2:5][C:4]1[CH:32]=[C:33]([Cl:35])[CH:34]=[C:2]([Cl:1])[CH:3]=1)[CH2:24][C:25]1[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=1)=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66616567HCID 66616567, compound

Product 1

HCID 585314683-(Aminomethyl)-N-(3,5-dichlorobenzyl)-N-(4-fluorobenzyl)benzamideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-((3,5-dichlorobenzyl)(4-fluorobenzyl)carbamoyl)benzylcarbamate (0.8 g, 1.55 mmol) in CH2Cl2 (8 mL) was added TFA (1.19 mL, 15.5 mmol). The reaction mixture was stirred at rt. for 4 h, concentrated and the residue was diluted with ethyl acetate and saturated aq NaHCO3 solution. The organic layer was separated, washed with brine, dried over MgSO4, and concentrated to give the product as a white solid (0.61 g, 95%). 1H NMR (DMSO-(d6): δ 7.52-7.06 (m, 11H), 4.65-4.40 (m, 4H), 3.72 (s, 2H); MS (ESI): [M+H]+=416.9.

Workup

  1. concentrationconcentrated
  2. additionthe residue was diluted with ethyl acetate and saturated aq NaHCO3 solution
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f394c57ac30849a6a3f0836c0f4b0f2e
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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