Cyclopropylamine → N-(4-Chloro-3-cyclopropylaminomethyl-benzyl)-3,3,3-trifluoro-propionamide

HRID 1715403Notes

Reaction equation

HRID 1715403 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[CH2:9][C:10]([F:13])([F:12])[F:11])=[CH:4][C:3]=1[CH:17]=O.[CH:19]1([NH2:22])[CH2:21][CH2:20]1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[CH2:9][C:10]([F:13])([F:12])[F:11])=[CH:4][C:3]=1[CH2:17][NH:22][CH:19]1[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 4311764Sodium borohydrideHCID 86622955N-(4-Chloro-3-formyl-benzyl)-3,3,3-trifluoro-propionamide

Product 1

HCID 67148430N-(4-Chloro-3-cyclopropylaminomethyl-benzyl)-3,3,3-trifluoro-propionamideYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-(4-chloro-3-formyl-benzyl)-3,3,3-trifluoro-propionamide (840 mg, 3.00 mmol) and cyclopropylamine (0.320 mL, 4.51 mmol) in MeOH (30 mL) was heated to reflux for 4 h. The mixture was allowed to cool to rt. NaBH4 (170 mg, 4.51 mmol) was added in portions. The mixture was stirred for 1 h, and the solvents were removed under reduced pressure. The residue was diluted with EtOAc, and the resulting mixture was washed with aq. sat. NaHCO3 and brine. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (CH2Cl2/MeOH 90:10) yielded the title compound (929 mg, 96%). LC-MS: tR=0.64 min; ES+: 321.05.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. customthe solvents were removed under reduced pressure
  4. additionThe residue was diluted with EtOAc
  5. washthe resulting mixture was washed with aq. sat. NaHCO3 and brine
  6. dry with materiallayer was dried over MgSO4
  7. filtrationfiltered
  8. customthe solvents were removed under reduced pressure
  9. customPurification of the crude by FC (CH2Cl2/MeOH 90:10)

Sources & evidence

ORD record
ord-71cd3e9d34ce4a63be11a1abb898a174
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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