Dimethylamine → HCID 23499563, compound

HRID 1836546Notes

Reaction equation

HRID 1836546 reaction equation
Cl[CH2:2][CH2:3][O:4][NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.[CH3:14][NH:15][CH3:16].[I-].[Na+]>C(#N)C.O1CCCC1.C(OCC)(=O)C>[CH3:14][N:15]([CH3:16])[CH2:2][CH2:3][O:4][NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1

Participants

7

Reactant 3

HCID 674DimethylamineHCID 5238Sodium IodideHCID 23499569HCID 23499569, compound

Product 1

HCID 23499563HCID 23499563, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

A solution of O-(2-chloroethyl)-N-(4-fluorobenzyl)-hydroxylamine (0.327 g, 1.6 mmol) in acetonitrile (2 ml) was treated with a solution of dimethylamine (16 mmol, 8 ml of a 2 M solution in tetrahydrofuran). Sodium iodide (0.06 g) was then added and the resulting mixture was sealed and heated at 55° C. for 16 h. The cooled mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate, brine and dried over anhydrous sodium sulphate. Evaporation of the solvent under reduced pressure yielded 0.310 g (91% yield) of the crude title hydroxylamine as a light brown oil which was used as such for the next step. 1HNMR 400 MHz (C6D6) δ (ppm): 2.19 (6H, s, NCH3), 2.47 (2H, t, J=6.1 Hz, CH2), 3.82 (2H, s, NCH2), 3.84 (2H, t, J=6.1 Hz, CH2), 6.9 (2H, m, aromatics), 7.11 (2H, m, aromatics).

Workup

  1. customthe resulting mixture was sealed
  2. washwashed with saturated sodium bicarbonate, brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-b0f2a21c68274e9d85a00582891c887c
Source dataset
uspto-grants-2004_08
Patent number
US06777440B2

Reaction notes

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