5-Tetralinylamine → HCID 178419826, compound

HRID 725905Notes

Reaction equation

HRID 725905 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 (5 ml) 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 resident 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.; H NMR (300 MHz, CDCl3) σ 7.05 (t, 1H) 6.82 (m, 2H); 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).

Workup

  1. customa thick-walled cap which
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. dissolutionThe resident 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
  11. customThe crude material was purified by flash chromatography (SiO2 ; 80:20 CHCl3 /CH3OH saturated with NH3)

Sources & evidence

ORD record
ord-7d86149d0cb941a48a65594bf1fee79b
Source dataset
uspto-grants-1998_01
Patent number
US05708015

Reaction notes

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