Lithium borohydride → 1-(4,4-Difluorocyclohexyl)methanamine

HRID 1483787Notes

Reaction equation

HRID 1483787 reaction equation
[F:1][C:2]1([F:11])[CH2:7][CH2:6][CH:5]([C:8]([NH2:10])=O)[CH2:4][CH2:3]1.[Li+].[BH4-]>C1COCC1>[F:1][C:2]1([F:11])[CH2:7][CH2:6][CH:5]([CH2:8][NH2:10])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 469422314,4-Difluorocyclohexanecarboxamide

Product 1

HCID 156044941-(4,4-Difluorocyclohexyl)methanamineYield 41.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 4,4-difluorocyclohexanecarboxamide (1.8 g, 13 mmol) in 100 mL THF was added LiBH4 (1.1 g, 50 mmol) under N2 stirred for overnight. Then the reaction mixture was refluxed for 4 h. After cooled to r.t, it was poured into ice-water slowly. After filtration, the product was extracted with DCM from filtrate. Combined organic layers washed with water, brine, dried over Na2SO4, filtered and condensed to afford compound (4,4-difluorocyclohexyl)methanamine (0.8 g, crude) as a colorless oil.

Workup

  1. temperatureThen the reaction mixture was refluxed for 4 h
  2. temperatureAfter cooled
  3. filtrationAfter filtration
  4. extractionthe product was extracted with DCM from filtrate
  5. washCombined organic layers washed with water, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customcondensed

Sources & evidence

ORD record
ord-e9cb286bbe8741b082d6959c1e7115d3
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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