Trifluoroacetic acid methylene chloride → N-(4-fluoro-2-methylphenyl)azetidin-3-amine

HRID 72425Notes

Reaction equation

HRID 72425 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]2)=[C:4]([CH3:20])[CH:3]=1.FC(F)(F)C(O)=O.ClCCl>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:12][NH:11][CH2:10]2)=[C:4]([CH3:20])[CH:3]=1

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 63303297Tert-butyl 3-((4-fluoro-2-methylphenyl)amino)azetidine-1-carboxylate

Product 1

HCID 65958632N-(4-fluoro-2-methylphenyl)azetidin-3-amineYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cooled solution of tert-butyl 3-((4-fluoro-2-methylphenyl)amino)azetidine-1-carboxylate (D30) (300 mg, 1.07 mmol) in dichloromethane (2 ml), a mixture of trifluoroacetic acid/dichloromethane (4.5 ml/1.5 ml) was added and the mixture stirred at room temperature for 1 h. Solvents were evaporated in vacuo and the resulting residue was purified by SPE-SCX cartridge (10 g). Collected ammonia fractions, after solvent evaporation afforded the title compound (D55) (0022/107/1) (190 mg)

Workup

  1. additionwas added
  2. customSolvents were evaporated in vacuo
  3. customthe resulting residue was purified by SPE-SCX cartridge (10 g)
  4. customCollected ammonia fractions, after solvent evaporation

Sources & evidence

ORD record
ord-5184a9bd74214ac4abe69de265c0ac4e
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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