Sodium borohydride → HCID 69216910, compound

HRID 1394285Notes

Reaction equation

HRID 1394285 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7][C:6](=[CH:9][C:10]#[N:11])[CH2:5][CH2:4]1.[BH4-].[Na+]>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[NH2:11][CH2:10][CH2:9][CH:6]1[CH2:5][CH2:4][C:3]([N:2]([CH3:1])[CH3:18])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 69216446HCID 69216446, compound

Product 1

HCID 69216910HCID 69216910, compound

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

(4-Dimethylamino-4-phenylcyclohexylidene)acetonitrile (1.16 g, 4.8 mmole) was dissolved in methanol (30 ml). Nickel(II) chloride hexahydrate (2.28 g, 9.6 mmole) was added to this solution. NaBH4 (1.82 mg, 48 mmole) was then added in portions with stirring and ice water cooling. Once addition was complete, stirring was continued at RT for 1 h. The resultant black nickel boride was removed by suction filtration after addition of 2M hydrochloric acid (15 ml) and washed with 2M hydrochloric acid (3×10 ml). The hydrochloric, aqueous-methanolic solution was reduced to half its volume in order to remove the methanol. The remaining aqueous phase was extracted with ether (3×10 ml) to remove neutral substances. The aqueous phase was then alkalised by addition of conc. aqueous ammonia solution and again extracted with ether (3×20 ml). The combined extracts were washed with saturated NaCl-solution (30 ml), dried over Na2SO4 and then evaporated. The resultant crude product could be purified by column chromatography [silica gel 60 (100 g); MeOH (1000 ml)]. However, this did not result in separation of the diastereoisomers. [4-(2-Aminoethyl)-1-phenylcyclohexyl]dimethylamine was obtained as a colorless oil in a yield of 643 mg (54%).

Workup

  1. additionOnce addition
  2. stirringstirring
  3. customThe resultant black nickel boride was removed by suction filtration
  4. additionafter addition of 2M hydrochloric acid (15 ml)
  5. washwashed with 2M hydrochloric acid (3×10 ml)
  6. customto remove the methanol
  7. extractionThe remaining aqueous phase was extracted with ether (3×10 ml)
  8. customto remove neutral substances
  9. additionThe aqueous phase was then alkalised by addition of conc. aqueous ammonia solution
  10. extractionagain extracted with ether (3×20 ml)
  11. washThe combined extracts were washed with saturated NaCl-solution (30 ml)
  12. dry with materialdried over Na2SO4
  13. customevaporated
  14. customThe resultant crude product could be purified by column chromatography [silica gel 60 (100 g); MeOH (1000 ml)]
  15. customHowever, this did not result in separation of the diastereoisomers

Sources & evidence

ORD record
ord-752d4f458fa344a4bb67502446c68084
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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