Cyclohexylamine → 4-[CYCLOHEXYLAMINO]-1-BUTANESULFONIC ACID

HRID 239808Notes

Reaction equation

HRID 239808 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:8]1[CH2:15][O:14][S:11](=[O:13])(=[O:12])[CH2:10][CH2:9]1>O1CCOCC1>[CH:1]1([NH:7][CH2:15][CH2:8][CH2:9][CH2:10][S:11]([OH:14])(=[O:13])=[O:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 154111,4-Butane sultone

Product 1

HCID 112070784-[CYCLOHEXYLAMINO]-1-BUTANESULFONIC ACIDYield 52%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of cyclohexylamine (2.0 g, 20.2 mmol) in 1,4-dioxane (13 mL) was added 1,4-butane sultone (2.61 g, 19.2 mmol). The solution was heated to reflux for 2 hours. The reaction was cooled to room temperature. The solid was collected by filtration, washed with acetone (2×20 mL) and dried in vacuo. Yield: 52%. 1H NMR (D2O, 500 MHz) δ ppm 2.95 (m, 3H), 2.81 (m, 2H), 1.92 (m, 2H), 1.67 (m, 6H), 1.52 (m, 1H), 1.18 (m, 4H), 1.02 (m, 1H). 13C (D2O, 125 MHz) δ ppm 57.32, 50.31, 44.01, 29.02, 24.84, 24.68, 24.07, 24.55. ES-MS 236 (M+1).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 2 hours
  3. filtrationThe solid was collected by filtration
  4. washwashed with acetone (2×20 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-d7bab6e8aa57430bae35dab90d5c529d
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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