Chloroform → (3,3,5,5-tetramethylcyclohexyl)methanamine hydrochloride

HRID 1636463Notes

Reaction equation

HRID 1636463 reaction equation
[N+:1]([CH2:4][C:5]1[CH2:10][C:9]([CH3:12])([CH3:11])[CH2:8][C:7]([CH3:14])([CH3:13])[CH:6]=1)([O-])=O.C(Cl)(Cl)[Cl:16]>C(O)C.[Pd]>[ClH:16].[CH3:11][C:9]1([CH3:12])[CH2:8][C:7]([CH3:13])([CH3:14])[CH2:6][CH:5]([CH2:4][NH2:1])[CH2:10]1

Participants

5

Reactant 2

HCID 6212ChloroformHCID 18783142HCID 18783142, compound

Product 1

HCID 18783159(3,3,5,5-tetramethylcyclohexyl)methanamine hydrochlorideYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-nitromethyl-3,3,5,5-tetramethylcyclohexene (6) (1.1 g, 5.63 mmol) in a mixture of ethanol (140 ml) and chloroform (2.8 ml) was hydrogenated over 10% Pd/C (280 mg) at 5 atm for 20 h, filtered and evaporated. The crude product was treated with ether, filtered and washed with ether to give 0.57 g (50%) of amine 5-26.

Workup

  1. filtrationfiltered
  2. customevaporated
  3. additionThe crude product was treated with ether
  4. filtrationfiltered
  5. washwashed with ether

Sources & evidence

ORD record
ord-adbf50842c5d4e8caa7997ac88cb4040
Source dataset
uspto-grants-2000_03
Patent number
US06034134

Reaction notes

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