Sodium borohydride → N1-(2,2,2-Trifluoroethyl)-1,4-benzenedimethanamine

HRID 1191009Notes

Reaction equation

HRID 1191009 reaction equation
[F:1][C:2]([F:15])([F:14])[CH2:3][NH:4][CH2:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.[BH4-].[Na+]>CO.O.O.O.O.O.O.[Co](Cl)Cl>[F:1][C:2]([F:14])([F:15])[CH2:3][NH:4][CH2:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][NH2:11])=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 24693315HCID 24693315, compound

Product 1

HCID 59828898N1-(2,2,2-Trifluoroethyl)-1,4-benzenedimethanamineYield 49%

Reagents, catalysts & solvents 2

HCID 517166Dichlorocobalt hexahydrateCatalystHCID 887MethanolSolvent

Procedure

Dissolve 4-[(2,2,2-trifluoroethylamino)-methyl]-benzonitrile (633 mg, 2.955 mmol) in methanol (22 mL). Add cobalt(II) chloride hexahydrate (1.41 g, 5.91 mmol) and stir for 20 min. Carefully add sodium borohydride (1.12 g, 29.55 mmol) in small batches and stir the mixture overnight. Quench the mixture with water and filter through celite, washing filtercake with chloroform:methanol:concentrated NH4OH (80:18:2). Concentrate the filtrate in vacuo, and partition the residue between water and chloroform. Extract the aqueous phase three times with chloroform iso-propanol (3:1). Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo. Purify by chromatography on silica gel (40 g, pre-packed cartridge) eluting with DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) (1:0 over 5 min, 19:1 over 5 min, 9:1 over 5 min, 85:15 over 5 min, 4:1; 50 mL/min) to obtain the title compound (316 mg, 49%). MS (ES+) m/z: 219 (M+H)+.

Workup

  1. customQuench the mixture with water
  2. filtrationfilter through celite
  3. washwashing filtercake with chloroform
  4. concentrationConcentrate the filtrate in vacuo
  5. custompartition the residue between water and chloroform
  6. extractionExtract the aqueous phase three times with chloroform iso-propanol (3:1)
  7. dry with materialDry the combined organic extracts over MgSO4
  8. filtrationfilter
  9. concentrationconcentrate in vacuo
  10. customPurify by chromatography on silica gel (40 g, pre-packed cartridge)
  11. washeluting with DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) (1:0 over 5 min, 19:1 over 5 min, 9:1 over 5 min, 85:15 over 5 min, 4:1; 50 mL/min)

Sources & evidence

ORD record
ord-697b4856e0a1416b8f825bd2961c7898
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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