Hydrochloric Acid → 5-[3-(Dimethylamino)propylamino]-1,3-dihydropyrrolo[4,3,2-de]isoquinoline

HRID 1284031Notes

Reaction equation

HRID 1284031 reaction equation
C(O[C:4]1[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]3[NH:14][CH:15]=[C:7]([C:8]=23)[CH2:6][N:5]=1)C.[CH3:16][N:17]([CH3:22])[CH2:18][CH2:19][CH2:20][NH2:21].Cl>C(O)C>[CH3:16][N:17]([CH3:22])[CH2:18][CH2:19][CH2:20][NH:21][C:4]1[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]3[NH:14][CH:15]=[C:7]([C:8]=23)[CH2:6][N:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 215155225-Ethoxy-1,3-dihydropyrrolo[4,3,2-de]isoquinoline

Product 1

HCID 30411115-[3-(Dimethylamino)propylamino]-1,3-dihydropyrrolo[4,3,2-de]isoquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 5-ethoxy-1,3-dihydropyrrolo[4,3,2-de]isoquinoline (5 g, 25 mmoles), described in Example 5, ethanol (50 ml), 3-(dimethylamino)propylamine (2.7 g, 26.4 mmoles) and conc. HCl (12.5 ml, 29 mmoles) in 50 ml of ethanol is heated at reflux for 7 hours. Some ethanol is removed by distillation, then ether and saturated HCl in ethanol (2 ml) is added. The precipitate is collected. Recrystallization for ethanol-ethyl acetate (a small amount of HCl in ethanol being added) gives the hydrochloride salt of the title compound, mp 289° - 290°C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 7 hours
  3. customSome ethanol is removed by distillation
  4. additionether and saturated HCl in ethanol (2 ml) is added
  5. customThe precipitate is collected
  6. customRecrystallization for ethanol-ethyl acetate (a small amount of HCl in ethanol being
  7. additionadded)

Sources & evidence

ORD record
ord-eeb47323c61044948fcd7cfb6b047e15
Source dataset
uspto-grants-1976_08
Patent number
US03978066

Reaction notes

Loading…