Hydrochloric Acid → N-(4-aminobutyl)methanesulfonamide hydrochloride

HRID 9404

Reaction equation

HRID 9404 reaction equation
[ClH:1].[CH3:2][S:3]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:11]C(=O)OC(C)(C)C)(=[O:5])=[O:4]>C(O)C>[ClH:1].[NH2:11][CH2:10][CH2:9][CH2:8][CH2:7][NH:6][S:3]([CH3:2])(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54180899Tert-butyl[4-(methanesulfonylamino)butyl]carbamate

Product 1

HCID 21984197N-(4-aminobutyl)methanesulfonamide hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of hydrochloric acid in ethanol was added to a solution of tert-butyl [4-(methanesulfonylamino)butyl]carbamate (18.9 g, 71.1 mmol) in ethanol (100 mL), and the reaction was heated at 100° C. for two hours. The solvent was removed under reduced pressure. A mixture of dichloromethane:hexanes was added to the resulting oil and removed under reduced pressure; this process was repeated several times. The residue was dried for three days under vacuum to provide 14.3 g of N-(4-aminobutyl)methanesulfonamide hydrochloride as a tan solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionA mixture of dichloromethane
  3. additionhexanes was added to the resulting oil
  4. customremoved under reduced pressure
  5. customThe residue was dried for three days under vacuum

Sources & evidence

ORD record
ord-3e1f5abfa6d942d1a82cf7baca23135b
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Linked notes

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