Sodium Carbonate → 5-[(2H-[1,3]Dioxolo[4,5-g]isoquinolin-5-yl)amino]pentan-1-ol

HRID 1579984Notes

Reaction equation

HRID 1579984 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]3[O:14][CH2:13][O:12][C:9]=3[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[OH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH2:21].C(=O)([O-])[O-].[Na+].[Na+]>CO>[OH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:2]1[C:11]2[C:6](=[CH:7][C:8]3[O:14][CH2:13][O:12][C:9]=3[CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 756345-Aminopentan-1-olHCID 21192459HCID 21192459, compound

Product 1

HCID 215647615-[(2H-[1,3]Dioxolo[4,5-g]isoquinolin-5-yl)amino]pentan-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.8 g. of 1-chloro-6,7-methylenedioxyisoquinoline and 5 g. of 5-hydroxypentylamine is heated at 140°C. for 5.5 hours. The resulting material is dissolved in methanol, sodium carbonate added and the resulting mixture refluxed for 15 minutes. The resulting mixture is filtered and evaporated in vacuo to an oil which is dissolved in chloroform. The resulting solution is evaporated in vacuo and the residue purified by chromatography over silica gel. The resulting oily product is then crystallized from ethanol/ethyl acetate and recrystallized from ethyl acetate/methanol to obtain 1-(5-hydroxypentyl)amino-6,7-methylenedioxyisoquinoline, m.p. 132.5°-134°C.

Workup

  1. additionA mixture of 1.8 g
  2. temperaturethe resulting mixture refluxed for 15 minutes
  3. filtrationThe resulting mixture is filtered
  4. customevaporated in vacuo to an oil which
  5. dissolutionis dissolved in chloroform
  6. customThe resulting solution is evaporated in vacuo
  7. customthe residue purified by chromatography over silica gel
  8. customThe resulting oily product is then crystallized from ethanol/ethyl acetate
  9. customrecrystallized from ethyl acetate/methanol

Sources & evidence

ORD record
ord-e4e8ef35787e4436bea47879c83bf3d8
Source dataset
uspto-grants-1976_01
Patent number
US03932412

Reaction notes

Loading…