Triethylamine → HCID 21521591, compound

HRID 918251Notes

Reaction equation

HRID 918251 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][CH3:9].C(N(CC)CC)C.Cl.Cl[C:19]([C:21]1[CH:22]=[N:23][C:24]([NH:27][C:28](=[O:30])[CH3:29])=[CH:25][CH:26]=1)=[O:20]>CN(C)C=O>[C:28]([NH:27][C:24]1[CH:25]=[CH:26][C:21]([C:19]([NH:1][CH2:2][CH:3]2[CH2:7][CH2:6][CH2:5][N:4]2[CH2:8][CH3:9])=[O:20])=[CH:22][N:23]=1)(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 21521580HCID 21521580, compound

Product 1

HCID 21521591HCID 21521591, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture of 12.8 g (0.1 mole) of 2-aminomethyl-1-ethyl pyrrolidine and 22.2 g (0.11 mole) of triethylamine was added at a temperature ≤20°C, to a solution of 23.5 g (0.1 mole) of 3-chlorocarbonyl-6-acetamido pyridine hydrochloride (itself prepared starting from 6-acetamido nicotinic acid) in 250 ml of anhydrous dimethylformamide. After the completion of the addition, the mixture was heated to 50°C for 1 hour then dimethylformamide was eliminated under reduced pressure. The oily residue was triturated with 200 ml of water and 100 ml of ether. The so-obtained base crystallized and there were obtained 17.4 g of 2-(6-acetamido nicotinamidomethyl)-1-ethyl pyrrolidine in the form of beige crystals melting (Kofler) at 162°-163°C. This compound was deacetylated according to the above described method and there were finally obtained 9.8 g of 2-(6-amino nicotinamidomethyl)-1-ethyl pyrrolidine, melting (Kofler) at 136°C.

Workup

  1. additionAfter the completion of the addition
  2. customThe oily residue was triturated with 200 ml of water and 100 ml of ether
  3. customThe so-obtained base crystallized

Sources & evidence

ORD record
ord-45822b4db6e24202a87f22872ab8e0fd
Source dataset
uspto-grants-1976_07
Patent number
US03970663

Reaction notes

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