1-Phenylcyclopropanemethanamine → Cyclohexaneethanamine, -bta-,-bta--dimethyl-

HRID 1612885Notes

Reaction equation

HRID 1612885 reaction equation
[C:1]1([C:7]2([CH2:10][NH2:11])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>C(O)(=O)C.[Pt]>[CH:1]1([C:7]([CH3:9])([CH3:8])[CH2:10][NH2:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 702871-PhenylcyclopropanemethanamineHCID 178418361HCID 178418361, compound

Product 1

HCID 19776368Cyclohexaneethanamine, -bta-,-bta--dimethyl-

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolvent2×

Procedure

{1-(1-Phenylcyclopropyl)}methylamine (205 mg, 1.1 mmole) was hydrogenated using platinum-black (410 mg) in 20 mL of acetic acid under 4 atmospheres of hydrogen for 3 days. The same conditions were repeated 3 times to complete the reaction. 2-Cyclohexyl-2-methylpropylamine was isolated as an acetic acid salt in quantitative yield. This material (28.5 mg, 0.12 mmole) was coupled with Example 4 (100 mg, 0.1 mmole) by the EDC and HOBT method followed by deprotection and purification to afford pure title compound (51 mg, 47%).

Workup

  1. customfor 3 days
  2. customthe reaction

Sources & evidence

ORD record
ord-2d2515b604614df188d6f598b196603b
Source dataset
uspto-grants-1993_03
Patent number
US05190922

Reaction notes

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