Benzylamine → HCID 15290425, compound

HRID 1757380Notes

Reaction equation

HRID 1757380 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([O:13][CH2:14][CH:15]1[O:19][C:18]([CH3:21])([CH3:20])[O:17][CH2:16]1)[CH:10]1[O:12][CH2:11]1>C(O)C>[CH2:1]([NH:8][CH2:11][CH:10]([OH:12])[CH2:9][O:13][CH2:14][CH:15]1[O:19][C:18]([CH3:21])([CH3:20])[O:17][CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 109212782,2-Dimethyl-4-{[(oxiran-2-yl)methoxy]methyl}-1,3-dioxolane

Product 1

HCID 15290425HCID 15290425, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A 500-ml three-necked flask equipped with a dropping funnel, thermometer and reflux condenser was charged with 174 ml (1.59 mol) of benzylamine and48.0 ml of ethanol. While heating and stirring the mixture at 80° C.in a nitrogen atmosphere, 20.3 g (0.11 mol) of 2,3-(dimethylmethylenedioxy)propyl glycidyl ether were added dropwise over2 hours. After completion of the addition, the heating and stirring were continued for an additional 1 hour under the same conditions. After the reaction mixture was concentrated under reduced pressure, the resulting residue was purified by flash chromatography on silica gel, thereby obtaining 20.4 g (yield: 64%) of the title compound (3a) as a pale yellow oil.

Workup

  1. customA 500-ml three-necked flask equipped with a dropping funnel
  2. temperaturethermometer and reflux condenser
  3. temperatureWhile heating
  4. additionAfter completion of the addition
  5. stirringthe heating and stirring
  6. concentrationAfter the reaction mixture was concentrated under reduced pressure
  7. customthe resulting residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-3f4d593e791b45f49a47aeb0b205f653
Source dataset
uspto-grants-1995_08
Patent number
US05446027

Reaction notes

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