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

HRID 1657263Notes

Reaction equation

HRID 1657263 reaction equation
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:11](O)[CH:10]=[CH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS(Cl)(=O)=O.C(N(CC)CC)C.[C:31]([NH2:35])([CH3:34])([CH3:33])[CH3:32]>CN(C)C=O.C(OCC)(=O)C.O>[C:31]([NH:35][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)([CH3:34])([CH3:33])[CH3:32]

Participants

8

Reactant 4

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 100371165,5-Diphenyl-2-cyclopenten-1-ol

Product 1

HCID 9796063N-t-butyl-4,4-diphenyl-2-cyclopentenylamine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5,5-diphenyl-2-cyclopenten-1-ol (0.20 g) in N,N-dimethylformamide (1 ml) were added methanesulfonyl chloride (0.35 ml) and triethylamine (0.60 ml) at 5° to 10° C. After being stirred for 1 hour, t-butylamine (1.78 ml) was added to the reaction mixture at 5° to 12° C. The reaction mixture was stirred for 3 days at room temperature. To the reaction mixture were added water and ethyl acetate. The organic layer was separated, washed with water, 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 (0.11 g).

Workup

  1. stirringThe reaction mixture was stirred for 3 days at room temperature
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. 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-352d18f36c804dceb5f7b368cb1e0493
Source dataset
uspto-grants-1993_10
Patent number
US05256824

Reaction notes

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