1,3-Propanediamine → HCID 21520954, compound

HRID 918366Notes

Reaction equation

HRID 918366 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH2:5].Cl.C(O[C:10]([CH:12]1[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2)=N)C.C([OH:27])C>>[NH:1]1[CH2:2][CH2:3][CH2:4][N:5]=[C:10]1[C:12]1([OH:27])[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2

Participants

4

Reactant 3

HCID 4281,3-PropanediamineHCID 702EthanolHCID 71398799Ethyl 9H-fluorene-9-carboximidate--hydrogen chloride (1/1)

Product 1

HCID 21520954HCID 21520954, compound

Conditions

Temperature
0 °C

Procedure

1,3-Diaminopropane (4.92 ml.) was added dropwise to a stirred, ice-cooled suspension of 9H-fluorene-9-carboximidic acid ethyl ester hydrochloride (14.8 g.) in absolute ethanol (100 ml.). The mixture was stirred for 30 minutes at 0°C, 30 minutes at room temperature and then heated under reflux overnight (16 hours). After evaporation of the ethanol the residue was dissolved in 2N hydrochloric acid, extracted once with ether and then basified (2N NaOH). The precipitate was filtered and recrystallised from isopropanol/ether to give the crude title compound (4.012 g.). The hydrochloride salt of the title compound crystallised from isopropanol/ethereal HCl, m.p. 242°-245°. Found: C, 67.6; H, 5.95; N, 9.05%. C17H16N2O.HCl requires C, 67.9; H, 5.7; N, 9.3%.

Workup

  1. temperaturecooled
  2. temperatureheated
  3. temperatureunder reflux overnight (16 hours)
  4. customAfter evaporation of the ethanol the residue
  5. dissolutionwas dissolved in 2N hydrochloric acid
  6. extractionextracted once with ether
  7. filtrationThe precipitate was filtered
  8. customrecrystallised from isopropanol/ether

Sources & evidence

ORD record
ord-e17c7084fa1c4209885b90821ed156d6
Source dataset
uspto-grants-1976_07
Patent number
US03971782

Reaction notes

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