Phthalic Anhydride → Ammonia

HRID 1578111Notes

Reaction equation

HRID 1578111 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[NH2:12][CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:23][CH:22]=2)[CH2:15][CH2:14]1>C(Cl)(Cl)Cl.C(O)(=O)C>[NH3:12].[NH:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:21]([CH2:20][CH2:19][N:16]2[CH2:15][CH2:14][CH:13]([N:12]3[C:1](=[O:11])[C:2]4[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:4]3=[O:6])[CH2:18][CH2:17]2)=[CH:22]1

Participants

6

Reactant 2

HCID 6811Phthalic AnhydrideHCID 2154154-Piperidinamine, 1-(2-(1H-indol-3-yl)ethyl)-, hydrate

Product 2

HCID 222AmmoniaHCID 20568893HCID 20568893, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

Phthalic anhydride (2.96 g, 0.02 mol, finely ground) and 4-amino-1-[2-(indol-3-yl)ethyl]piperidine (4.86 g, 0.02 mol) were suspended in chloroform (40 cm3) and the suspension stirred at room temperature overnight. The solvent was then evaporated and acetic anhydride (40 cm3) added to the residue. This mixture was heated on a steam bath for 2 hours then the solvent removed in vacuo to give a glassy solid which was dissolved in very dilute aqueous acetic acid. Basification of the solution with 0.880 ammonia gave the title compound as a gum which solidified on trituration with methanol. (4.31 g, 57.8%). A suspension of the base in ethanolic HCl was stirred overnight to give the hydrochloride, mp. 252°-260° after extensive decomposition above 240° C.

Workup

  1. customThe solvent was then evaporated
  2. additionacetic anhydride (40 cm3) added to the residue
  3. temperatureThis mixture was heated on a steam bath for 2 hours
  4. customthe solvent removed in vacuo
  5. customto give a glassy solid which

Sources & evidence

ORD record
ord-ced2f995e5fb4ccc8a28e614ff735c55
Source dataset
uspto-grants-1981_09
Patent number
US04291042

Reaction notes

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