2-Methyl-1-(naphthalen-2-yl)propan-2-amine--hydrogen chloride (1/1) → 6-(1,1-Dimethyl-1-aminoethyl)-1,2,3,4-tetrahydronaphthalene hydrochloride

HRID 2215282Notes

Reaction equation

HRID 2215282 reaction equation
[ClH:1].[CH3:2][C:3]([CH3:16])([NH2:15])[CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[CH:10][CH:9]=[CH:8]2>C(O)(=O)C.O=[Pt]=O>[ClH:1].[CH3:2][C:3]([CH3:16])([NH2:15])[CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH2:11][CH2:10][CH2:9][CH2:8]2

Participants

4

Reactant 1

HCID 532499312-Methyl-1-(naphthalen-2-yl)propan-2-amine--hydrogen chloride (1/1)

Product 1

HCID 696175266-(1,1-Dimethyl-1-aminoethyl)-1,2,3,4-tetrahydronaphthalene hydrochlorideYield 85%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 1.0 g (4.2 mmol) of 6-(1,1-dimethyl-1-aminoethyl)naphthalene hydrochloride in glacial acetic acid (100 mL) was treated under Argon atmosphere with PtO2 (350 mg). The mixture was hydrogenated in a Parr shaker at 50 psi for 1 h. and filtered through a plug of celite. The filtrate was concentrated in vacuo and concentrated from ether. The residue was triturated with ether and the white crystalline solid (850 mg, 85% yield) was collected, washed with ether and dried. MS(ES) m/z 204.2(M+H)+; Elemental analysis: theoretical for C14H21N.HCl.1/2 H2O: C, 67.58; H, 9.31; N, 5.63. found: C, 67.51; H, 9.31; N, 5.63.

Workup

  1. filtrationfiltered through a plug of celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. concentrationconcentrated from ether
  4. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-d0579c35fbb44373a7aebe5c794cc9fb
Source dataset
uspto-grants-2006_09
Patent number
US07109238B2

Reaction notes

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