Cyclohexylamine → 4-(Cyclohexylamino)butane-2-sulfonic acid

HRID 239800Notes

Reaction equation

HRID 239800 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:8][CH:9]1[S:13](=[O:15])(=[O:14])[O:12][CH2:11][CH2:10]1>O1CCCC1>[CH:1]1([NH:7][CH2:11][CH2:10][CH:9]([S:13]([OH:15])(=[O:14])=[O:12])[CH3:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 707161,2-Oxathiolane, 3-methyl-, 2,2-dioxide

Product 1

HCID 589318334-(Cyclohexylamino)butane-2-sulfonic acidYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of cyclohexylamine (1.50 g, 15.1 mmol) in tetrahydrofuran (15 mL) was added 2,4-butane sultone (2.04 g, 14.4 mmol). The solution stirred at reflux for 2 hours. The reaction was cooled to room temperature. The solid was collected by filtration and dried in vacuo. Yield: 59%. 1H NMR (DMSO, 500 MHz) δ ppm 8.50 (s (broad), 1H), 3.02 (m, 2H), 2.93 (m, 1H), 2.60 (m, 1H), 1.93 (m, 3H), 1.75 (m, 3H), 1.57 (m, 1H), 1.21 (m, 4H), 1.11 (m, 4H). 13C (DMSO, 125 MHz) δ ppm 56.23, 53.20, 43.09, 29.54, 29.41, 29.39, 25.40, 24.42, 17.23. ES-MS 234 (M−1).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid was collected by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-876a7a95927849deb4ab48a1184c4cdb
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

Loading…