Ammonia → 7-Azatryptamine

HRID 1593516Notes

Reaction equation

HRID 1593516 reaction equation
Cl[CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[I-].[Na+].[NH3:15]>CO>[NH:6]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:12]2[C:4]([CH2:3][CH2:2][NH2:15])=[CH:5]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5238Sodium IodideHCID 13285353HCID 13285353, compound

Product 1

HCID 54881977-Azatryptamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-(2-Chloroethyl)-1H-pyrrolo[2,3-b]pyridine (4.0 g) and sodium iodide (3.2 g, 0.95 eq.) in a solution of ammonia in methanol (7 N, 20 mL) is heated to 60° C. in a Fischer-Porter sealed pressure bottle for 48 h. The bottle is cooled, opened cautiously and the solvent removed in vacuo. The resultant residue is recrystallized from THF to give the title ethylamine compound as a tan solid, 4.8 g, identified by HPLC and mass spectral analyses.

Workup

  1. customsealed pressure bottle for 48 h
  2. temperatureThe bottle is cooled
  3. customthe solvent removed in vacuo
  4. customThe resultant residue is recrystallized from THF

Sources & evidence

ORD record
ord-b07198e899884a3090e0ca153e172f6f
Source dataset
uspto-grants-2007_11
Patent number
US07297705B2

Reaction notes

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