N-Benzyl-3-pyrrolidinol Chemical Properties

Boiling point:

113-115 °C2 mm Hg(lit.)

Density 

1.07 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.548(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

14.82±0.20(Predicted)

form 

clear liquid

color 

Colorless to Light yellow to Light orange

BRN 

6039

InChI

InChI=1S/C11H15NO/c13-11-6-7-12(9-11)8-10-4-2-1-3-5-10/h1-5,11,13H,6-9H2

InChIKey

YQMXOIAIYXXXEE-UHFFFAOYSA-N

SMILES

N1(CC2=CC=CC=C2)CCC(O)C1

CAS DataBase Reference

775-15-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,Xi

Risk Statements 

25-36/37/38

Safety Statements 

26-36

RIDADR 

UN 2810 6.1/PG 3

WGK Germany 

1

F 

10-34

HazardClass 

6.1

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

N-Benzyl-3-pyrrolidinol Usage And Synthesis

Uses

1-Benzyl-3-pyrrolidinol was used in preparation of:

• potent calcium antagonist, 1-benzyl-3-pyrrolidinyl methyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• (3R)-1-benzyl-3-methanesulfonyloxy pyrrolidine

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 4296, 1986 DOI: 10.1021/jo00372a038

Synthesis

The present embodiment is a method for the preparation of N-benzyl-3-hydroxypyrrolidine, which was carried out as follows: 250 g of 40 wt% aqueous benzylamine solution was added to a 500 mL four-necked flask and cooled to 10 °C. In an ice water bath, 102 g of 1,4-dichloro-2-butanol was added dropwise while stirring and the temperature was controlled at 15 °C. After the dropwise addition was completed in about 15 min, the system was transferred to a 500 mL autoclave, sealed, evacuated to a pressure of 1.0 ± 0.1 MPa, and simultaneously heated to 120 ± 2 °C, and the reaction was stirred for about 10 h. The disappearance of the raw material was monitored by GC. At the end of the reaction, cooled to room temperature, the material was discharged, 110g of sodium hydroxide was added in batches, and the temperature was controlled to be lower than 50°C in order to release the methylamine gas and precipitate a large amount of white solids, stirring for 1h. After filtration, the filtrate was stratified, and the upper organic phase was treated with 100mL of ethanol and 18g of anhydrous magnesium sulphate, stirring for 2-3h. It was filtered again, and the filtrate was concentrated under vacuum to get a yellow transparent oily liquid, and finally By vacuum distillation, 46.7 g of colorless and transparent N-benzyl-3-hydroxypyrrolidine was obtained with 64.8% yield and 99.3% purity (HPLC).

References

[1] Patent: CN106631956, 2017, A. Location in patent: Paragraph 0022; 0023; 0024; 0025; 0026; 0027

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