Hydrazine hydrate (1:1) → 4-[3-Aminopropoxy]-N,N-dimethylbenzeneethanamine

HRID 325686

Reaction equation

HRID 325686 reaction equation
[CH3:1][N:2]([CH3:26])[CH2:3][CH2:4][C:5]1[CH:25]=[CH:24][C:8]([O:9][CH2:10][CH2:11][CH2:12][N:13]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:7][CH:6]=1.O.NN>C(O)C>[NH2:13][CH2:12][CH2:11][CH2:10][O:9][C:8]1[CH:7]=[CH:6][C:5]([CH2:4][CH2:3][N:2]([CH3:26])[CH3:1])=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 212975672-[3-[4-[2-(Dimethylamino)ethyl]phenoxy]propyl]-1H-isoindole-1,3-(2H)-dione

Product 1

HCID 212975554-[3-Aminopropoxy]-N,N-dimethylbenzeneethanamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-[3-[4-[2-(Dimethylamino)ethyl]phenoxy]propyl]-1H-isoindole-1,3-(2H)-dione (2.1 g) and hydrazine hydrate (1.2 ml) were heated at reflux in ethanol for 4 h. The solvent was evaporated and the residue was distilled to give the title compound as a clear yellow oil b.p. 170° (0.1 mm). TLC silica; ethyl acetate:water:isopropanol:0.88 ammonia 25:8:15:2; Rf 0.35.

Workup

  1. customThe solvent was evaporated
  2. distillationthe residue was distilled

Sources & evidence

ORD record
ord-a7dd293f0c334bf2a6bbdb2de53afc76
Source dataset
uspto-grants-1984_04
Patent number
US04442110

Linked notes

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