Hydroxylamine → Methylamine

HRID 1656387Notes

Reaction equation

HRID 1656387 reaction equation
NO.[CH3:3]S(Cl)(=O)=O.[CH2:8]([N:10]([CH2:13][CH3:14])CC)[CH3:9]>>[CH3:8][NH2:10].[CH2:8]([NH2:10])[CH3:9].[CH2:13]([NH2:10])[CH2:14][CH3:3]

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 3

HCID 6329MethylamineHCID 6341EthylamineHCID 7852Propylamine

Procedure

Conversion of the aminoalcohol to a diamine (II) can be done with methanesulfonyl chloride in the presence of a base such as triethylamine at a temperature between about 0° and 5° C. Further treatment of the resulting sulfonate with an excess of an alcoholic solution of an amine (RNH2) such as methylamine, ethylamine or n-propylamine, at a temperature between about 70° and 80° C. yields a diamine (II).

Sources & evidence

ORD record
ord-b2375b6319eb48878ef12538573c27b2
Source dataset
uspto-grants-1993_10
Patent number
US05254569

Reaction notes

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