1-(Prop-2-yn-1-yl)pyrrolidine Chemical Properties

Boiling point:

186°C(lit.)

Density 

1.0009 g/cm3

refractive index 

1.4730 to 1.4770

storage temp. 

2-8°C

form 

clear liquid

pka

5.14±0.10(Predicted)

color 

Colorless to Light yellow

InChI

InChI=1S/C7H11NO/c1-2-3-8-4-6-9-7-5-8/h1H,3-7H2

InChIKey

OKDZHAQIKCVKFE-UHFFFAOYSA-N

SMILES

N1(CC#C)CCOCC1

Safety Information

RIDADR 

UN 1993 3/PG III

HazardClass 

3

PackingGroup 

III

HS Code 

2934999090

1-(Prop-2-yn-1-yl)pyrrolidine Usage And Synthesis

Uses

1-(Prop-2-yn-1-yl)pyrrolidine is used as an intermediate in organic synthesis or pharmaceuticals.

Synthesis

The general procedure for the synthesis of 1-(4-morpholinyl)-2-propyne from morpholine and 3-bromopropargyl was as follows: morpholine (100 mL, 1.148 mol) was dissolved in methanol (1 L) and cooled in an ice bath under nitrogen protection. Subsequently, potassium carbonate (120 g, 0.63 mol) and propargyl bromide (124 mL, 1.148 mol) were sequentially added under ice bath stirring conditions. The reaction mixture was continued to be stirred without cooling for 4 hours. After completion of the reaction, the resulting white suspension was filtered through filter paper and the solid residue was washed with methanol (100 mL). The filtrates were combined and methanol was removed by careful evaporation. The white precipitate obtained was suspended in dichloromethane (400 mL), filtered again through filter paper and the solvent was carefully evaporated. Finally, the product was distilled under reduced pressure at 60 °C and 16 mbar to give 100 g of colorless oily product in 70% yield.

References

[1] Journal of Organometallic Chemistry, 1983, vol. 244, # 4, p. 311 - 318
[2] Journal of Combinatorial Chemistry, 2010, vol. 12, # 4, p. 491 - 496
[3] Journal of the American Chemical Society, 2014, vol. 136, # 12, p. 4740 - 4745
[4] Green Chemistry, 2009, vol. 11, # 8, p. 1115 - 1120
[5] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1982, p. 1459 - 1466

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