Diisopropyl Ether → N-(1-Benzyl-3-pyrrolidinyl)-3,4,5-trimethoxybenzamide

HRID 1659153Notes

Reaction equation

HRID 1659153 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:3]1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[C:19](N=[N+]=[N-])=[O:20].C(OC(C)C)(C)C>C1C=CC=CC=1>[CH2:7]([N:4]1[CH2:5][CH2:6][CH:2]([NH:1][C:19](=[O:20])[C:18]2[CH:17]=[C:16]([O:15][CH3:14])[C:26]([O:27][CH3:28])=[C:25]([O:29][CH3:30])[CH:24]=2)[CH2:3]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 27566131-Benzyl-3-aminopyrrolidineHCID 149508103,4,5-Trimethoxybenzoyl azide

Product 1

HCID 12898835N-(1-Benzyl-3-pyrrolidinyl)-3,4,5-trimethoxybenzamideYield 60%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1.8 g. (0.01 mole) of 3-amino-1-benzylpyrrolidine, 2.4 g. (0.01 mole) of 3,4,5-trimethoxybenzoyl azide, and 25 ml. of dry benzene was stirred 16 hours at room temperature followed by stirring for one hour at about 60°C. The mixture was cooled and 50 ml. of isopropyl ether added to the mixture. The crude crystalline product was separated by filtration and recrystallized from ethyl acetate-isopropyl ether mixture, giving 2.2 g. (60% yield). The melting point of the product after a second recrystallization from the same solvent was 128°-129°C.

Workup

  1. additionA mixture of 1.8 g
  2. temperatureThe mixture was cooled
  3. customThe crude crystalline product was separated by filtration
  4. customrecrystallized from ethyl acetate-isopropyl ether mixture
  5. customgiving 2.2 g
  6. customThe melting point of the product after a second recrystallization from the same solvent
  7. customwas 128°-129°C.

Sources & evidence

ORD record
ord-7c51473b2ae84dbe9814e614d9e696eb
Source dataset
uspto-grants-1976_06
Patent number
US03966957

Reaction notes

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