Sodium sulfate decahydrate → 1-(3-Tert-butyl-phenyl)-4-methylene-cyclohexylamine

HRID 132106Notes

Reaction equation

HRID 132106 reaction equation
[N:1]([C:4]1([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:12]=2)[CH2:9][CH2:8][C:7](=[CH2:10])[CH2:6][CH2:5]1)=[N+]=[N-].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)C>[C:17]([C:13]1[CH:12]=[C:11]([C:4]2([NH2:1])[CH2:5][CH2:6][C:7](=[CH2:10])[CH2:8][CH2:9]2)[CH:16]=[CH:15][CH:14]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 597337741-(1-Azido-4-methylene-cyclohexyl)-3-tert-butyl-benzene

Product 1

HCID 597337471-(3-Tert-butyl-phenyl)-4-methylene-cyclohexylamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1-(1-azido-4-methylene-cyclohexyl)-3-tert-butyl-benzene (820 mg, 3.04 mmol) in diethyl ether (10 mL) was added to a heterogeneous mixture of lithium aluminum hydride (510 mg, 13.4 mmol) in diethyl ether (10 mL) and was placed into a preheated oil bath at 40° C. After heating at reflux for 24 h, the solution was cooled to ambient temperature, and celite and sodium sulfate decahydrate was added. After stirring for 1 h, the heterogeneous mixture was filtered through celite to yield 1-(3-tert-butyl-phenyl)-4-methylene-cyclohexylamine.

Workup

  1. customwas placed into a preheated oil bath at 40° C
  2. temperatureAfter heating
  3. temperatureat reflux for 24 h
  4. filtrationthe heterogeneous mixture was filtered through celite

Sources & evidence

ORD record
ord-901a0a0c57094c61b84d5f4ca2306cc5
Source dataset
uspto-grants-2008_06
Patent number
US07385085B2

Reaction notes

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