Ethanol → N-Cycloheptyl-[(2-fluorenyl)methyl]amine

HRID 37639

Reaction equation

HRID 37639 reaction equation
[CH:1]([C:3]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6][C:5]=2[CH:4]=1)=O.[CH:16]1([NH2:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(O)C.[BH4-].[Na+]>O>[CH:16]1([NH:23][CH2:1][C:3]2[CH:15]=[CH:14][C:13]3[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[CH2:6][C:5]=3[CH:4]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 702EthanolHCID 2899CycloheptylamineHCID 34804Fluorene-2-carboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 15284282N-Cycloheptyl-[(2-fluorenyl)methyl]amineYield 92.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Formylfluorene (2.27 g, 11.7 mmol) and cycloheptylamine (1.39 g, 12.3 mmol) were heated together at 120° C. for 14 hrs. After cooling, the reaction mixture was distilled under reduced pressure. Then, ethanol (30 ml) and sodium borohydride (0.44 g, 11.7 mmol) were added to the residue and the mixture was stirred for 0.5 hr. The mixture was then diluted with water (100 ml) and extracted with chloroform (80 ml×2 times). The organic layer was dried over anhydrous magnesiumsulfate. The solvent was then distilled off under reduced pressure to give 3.15 g of a pale yellow solid residue.

Workup

  1. temperatureAfter cooling
  2. distillationthe reaction mixture was distilled under reduced pressure
  3. extractionextracted with chloroform (80 ml×2 times)
  4. dry with materialThe organic layer was dried over anhydrous magnesiumsulfate
  5. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-cbaaad8d1e694595b94773f37e5b580e
Source dataset
uspto-grants-1995_05
Patent number
US05420348

Linked notes

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