Dimethylformamide → HCID 19848617, compound

HRID 1608206Notes

Reaction equation

HRID 1608206 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14]Cl)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:16]=[N+:17]=[N-:18].[Na+].CN(C)C=O>O>[N:16]([CH2:14][CH:10]1[O:11][CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9]1)=[N+:17]=[N-:18]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 28015624-Benzyl-2-(chloromethyl)morpholine

Product 1

HCID 19848617HCID 19848617, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4-benzyl-2-chloromethylmorpholine (15.0 g), sodium azide (8.6 g), and dimethylformamide (150 ml) is stirred at 130° C. for 2 hours. The reaction mixture is diluted with water and extracted with diethyl ether. The organic layer is washed successively with water and saturated aqueous sodium chloride solution, and dried over magnesium sulfate. The solvent is distilled off under reduced pressure to give 2-azidomethyl-4-benzylmorpholine (15 g) as an oil.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic layer is washed successively with water and saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-dfe55ac9d734434aa98ae35a3c160b17
Source dataset
uspto-grants-1989_09
Patent number
US04870074

Reaction notes

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