Nitrogen → Ethanol, 2-[2-(1-pyrrolidinyl)ethoxy]-

HRID 714206Notes

Reaction equation

HRID 714206 reaction equation
N#N.[NH:3]1[CH2:7][CH2:6][CH2:5][CH2:4]1.Cl[CH2:9][CH2:10][O:11][CH2:12][CH2:13][OH:14].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[N:3]1([CH2:9][CH2:10][O:11][CH2:12][CH2:13][OH:14])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 123612-(Chloroethoxy)ethanolHCID 31268Pyrrolidine

Product 1

HCID 10080651Ethanol, 2-[2-(1-pyrrolidinyl)ethoxy]-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of pyrrolidine (0.35 mL, 4.22 mmol) and 2-(2-chloroethoxy)ethanol (0.45 mL, 4.22 mmol) in dry toluene (7 mL) was added K2CO3 (3.21 g, 23.20 mmol) at rt followed by KI (70 mg, 0.42 mmol). The reaction mixture was stirred at reflux for 15 h. The mixture was filtered and the filtrate concentrated under reduced pressure to give crude 2-(2-(pyrrolidin-1-yl)ethoxy)ethanol as a yellow oil. TLC:rf (90:10:0.5 CH2Cl2-MeOH—NH4OH)=0.17.

Workup

  1. temperatureat reflux for 15 h
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-841fbc258c874124bfddd704413469aa
Source dataset
uspto-grants-2015_11
Patent number
US09187435B2

Reaction notes

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