5-Tetralinylamine → HCID 178419826, compound

HRID 1656007Notes

Reaction equation

HRID 1656007 reaction equation
[C:1]1([NH2:11])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH:12]1[CH2:16][CH2:15][N:14]=[C:13]1S(O)(=O)=O>CC#N>[C:1]1([N:11]=[C:13]2[NH:14][CH2:15][CH2:16][NH:12]2)[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 166715-TetralinylamineHCID 2745614,5-dihydro-1H-imidazole-2-sulfonic acid2×

Product 1

HCID 178419826HCID 178419826, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
155 °C

Procedure

5,6,7,8-Tetrahydro-1-naphthylamine (Aldrich, 159 mg, 1.06 mmol), imidazoline-2-sulfonic acid (147.0 mg, 1.0 mmol, Compound 7 obtained as described above) and CH3CN (5ml) were placed in a thick-walled cap which was sealed with a TEFLON™ screw and heated to 155° C. for 1.25 hours The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was dissolved in CHCl3 and washed with aq. 1N NaOH (to pH 13). The organic layer was separated, washed with brine, dried over Na2CO3 and concentrated in vacuo to yield a brown oil The crude material was purified by flash chromatography (SiO2 ; 80:20 CHCl3 /CH3OH saturated with NH3) to yield 29.5 mg (14%) of the title compound as a white solid: mp 138°-141° C.; 1H NMR (300 MHz, CDCl3 ) & 7.05 (t, 1H) 6.82 (m, 2 H); 5.41 (br, 2H); 3.50 (s, 4H); 2.79 (m, 2H); 2.62 (m, 2H); 1.80 (m, 4H); Mass spectrum m/e 214.1339 (C13H16N3 requires 214.1344). Alternatively and preferably alcohols, most preferably isobutanol, are used instead of CH3CN in this reaction

Workup

  1. customa thick-walled cap which
  2. temperaturewas cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in CHCl3
  5. washwashed with aq. 1N NaOH (to pH 13)
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried over Na2CO3
  9. concentrationconcentrated in vacuo
  10. customto yield a brown oil The crude material
  11. customwas purified by flash chromatography (SiO2 ; 80:20 CHCl3 /CH3OH saturated with NH3)

Sources & evidence

ORD record
ord-00840f1cae4b444b8461b6c613d27ee0
Source dataset
uspto-grants-1993_10
Patent number
US05252595

Reaction notes

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