Sodium Hydroxide → HCID 14293583, compound

HRID 500457Notes

Reaction equation

HRID 500457 reaction equation
[CH:1]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C>[CH:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 138161892-Cyclohexylquinoline

Product 1

HCID 14293583HCID 14293583, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-cyclohexylquinoline (2.66 g, 12.61 mmol) in glacial acetic acid (25 ml) was treated with sodium cyanoborohydride (2.38 g, 37.82 mmol) and stirred at room temperature for 4 h and then 40° C. for 18 h. The mixture was then treated with 2 M sodium hydroxide (200 ml), stirred for 30 min and extracted into ethyl acetate (3×100 ml). The combined organic layers were then washed with water (3×100 ml), dried with sodium sulfate, evaporated under reduced pressure and the residue purified by flash chromatography eluting with 0-3% (v/v) ethyl acetate in isohexane to afford 2-cyclohexyl-1,2,3,4-tetrahydroquinoline as a yellow oil (1.61 g, 7.49 mmol).

Workup

  1. wait40° C. for 18 h
  2. stirringstirred for 30 min
  3. extractionextracted into ethyl acetate (3×100 ml)
  4. washThe combined organic layers were then washed with water (3×100 ml)
  5. dry with materialdried with sodium sulfate
  6. customevaporated under reduced pressure
  7. customthe residue purified by flash chromatography
  8. washeluting with 0-3% (v/v) ethyl acetate in isohexane

Sources & evidence

ORD record
ord-90cb72150ae244878a311625d7e68c0d
Source dataset
uspto-grants-2010_08
Patent number
US07772227B2

Reaction notes

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