Cadaverine → 6-(5-aminopentyl)-5,6-dihydro-5,11-diketo-11H-indeno[1,2-c]isoquinoline hydrochloride

HRID 72840

Reaction equation

HRID 72840 reaction equation
[CH:1]1[C:6]2[C:7]3[C:18](=O)[C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[C:8]=3[O:9][C:10](=[O:11])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH2:26].C(Cl)(Cl)[Cl:28]>>[ClH:28].[NH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]1[C:7]2[C:6]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[C:10](=[O:11])[C:18]=2[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:8]1=[O:9]

Participants

4

Reactant 3

HCID 273CadaverineHCID 6212ChloroformHCID 265728Indeno(1,2-c)isochromene-5,11-dione

Product 1

HCID 162212016-(5-aminopentyl)-5,6-dihydro-5,11-diketo-11H-indeno[1,2-c]isoquinoline hydrochlorideYield 82%

Procedure

Benz[d]indeno[1,2-b]pyran-5,11-dione (4d) (0.100 g, 0.403 mmol) was treated with 1,5-diaminopentane (0.206 g, 2.014 mmol) in CHCl3 (40 mL) and the reaction mixture was heated at reflux for 16 h. The reaction mixture was allowed to cool to room temperature and washed with water (3×15 mL). The solution was dried over sodium sulfate, filtered, and treated with 2 M HCl in Et2O (5 mL). After 30 min, the reaction mixture was filtered and the filter pad was washed with CHCl3 (50 mL) and hexanes (50 mL) to provide an orange solid (0.122 g, 82%): mp 265-268° C. IR (film) 3432, 3077, 2856, 1707, 1635, 1611, 1549, and 1504 cm−1; 1H NMR (CDCl3) δ 8.59 (d, J=8.1 Hz, 1H), 8.23 (d, J=8.1 Hz, 1H), 7.85-7.80 (m, 3H), 7.74 (d, J=7.4 Hz, 1H), 7.63-7.51 (m, 4H), 4.52 (t, J=7.3 Hz, 2H), 2.81 (m, 2H), 1.83 (m, 2H) 1.65-1.52 (m, 4H); ESIMS m/z (rel intensity) 333 (MH+, 100). Anal. (C21H21ClN2O2.0.75H2O) C, H, N.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. washwashed with water (3×15 mL)
  4. dry with materialThe solution was dried over sodium sulfate
  5. filtrationfiltered
  6. additiontreated with 2 M HCl in Et2O (5 mL)
  7. filtrationthe reaction mixture was filtered
  8. washthe filter pad was washed with CHCl3 (50 mL) and hexanes (50 mL)

Sources & evidence

ORD record
ord-1896206c22c64f498a32c3cc73760910
Source dataset
uspto-grants-2014_09
Patent number
US08829022B2

Linked notes

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