Tert-Butylamine → N-t-butyl-4,4-diphenyl-2-cyclopentenylamine

HRID 1657289Notes

Reaction equation

HRID 1657289 reaction equation
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][C:10](=O)[CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:19]([NH2:23])([CH3:22])([CH3:21])[CH3:20].[BH4-].[Na+].[OH-].[Na+]>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl.CO>[C:19]([NH:23][CH:10]1[CH2:11][C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=[CH:9]1)([CH3:22])([CH3:21])[CH3:20].[C:19]([NH:23][CH:10]1[CH2:9][CH2:8][C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:11]1)([CH3:22])([CH3:21])[CH3:20]

Participants

9

Reactant 4

HCID 6385Tert-ButylamineHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 108898542-Cyclopenten-1-one, 4,4-diphenyl-

Product 2

HCID 9796063N-t-butyl-4,4-diphenyl-2-cyclopentenylamineHCID 10379659N-t-butyl-3,3-diphenylcyclopentylamine

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4,4-diphenyl-2-cyclopenten-1-one (0.40 g), t-butylamine (0.75 g) in methylene chloride (9 ml) was added dropwise a solution of titanium tetrachloride (0.50 g) in methylene chloride (5 ml) at -70° C. to -60° C. After being stirred for 2 hours, sodium borohydride (0.35 g) and methanol (6 ml) were added successively at 0° C. After being stirred for 0.5 hour, the precipitate was filtered off using celite and the filtrate was condensed under reduced pressure. To the residue, 1N sodium hydroxide aqueous solution was added and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol as an eluent to give N-t-butyl-4,4-diphenyl-2-cyclopentenylamine (0.13 g) and N-t-butyl-3,3-diphenylcyclopentylamine (0.19 g) respectively.

Workup

  1. stirringAfter being stirred for 0.5 hour
  2. filtrationthe precipitate was filtered off
  3. customcondensed under reduced pressure
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol as an eluent

Sources & evidence

ORD record
ord-070b448fd8434e7b9d74b4b56b438bd6
Source dataset
uspto-grants-1993_10
Patent number
US05256824

Reaction notes

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