HCID 20385850, compound → 3-tert-Butyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline

HRID 46815Notes

Reaction equation

HRID 46815 reaction equation
[C:1]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pt]=O.C(O)(=O)C>[C:1]([CH:5]1[CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][NH:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 20385850HCID 20385850, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 203858453-tert-Butyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 28.5 g. (0.11 mole) of 3-tert. butyl-4-phenyl isoquinoline, 2.85 g. platinum oxide and 300 ml. of acetic acid is hydrogenated at room temperature and 50 psi until two equivalents of hydrogen are absorbed. The catalyst is filtered off and the acetic acid is evaporated in vacuo. The residue is dissolved in ether, washed with 50% sodium hydroxide, water and saturated sodium fluoride solution, dried over magnesium sulfate, filtered and evaporated. The residue is crystallized from petroleum ether to give 3-tert.butyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline; m.p. 79°-81° C.

Workup

  1. additionA mixture of 28.5 g
  2. customis hydrogenated at room temperature
  3. filtrationThe catalyst is filtered off
  4. customthe acetic acid is evaporated in vacuo
  5. dissolutionThe residue is dissolved in ether
  6. washwashed with 50% sodium hydroxide, water and saturated sodium fluoride solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue is crystallized from petroleum ether

Sources & evidence

ORD record
ord-fd07a8ad729a4f4ca1a0deb116774db6
Source dataset
uspto-grants-1979_11
Patent number
US04175191

Reaction notes

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