Furfurylamine → HCID 86702149, compound

HRID 1776223Notes

Reaction equation

HRID 1776223 reaction equation
[CH2:1]([NH2:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[CH:8]1([S:14](Cl)(=[O:16])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>N1C=CC=CC=1>[O:6]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:1][NH:7][S:14]([CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 3438FurfurylamineHCID 237554Cyclohexanesulfonyl chloride

Product 1

HCID 86702149HCID 86702149, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of furfurylamine (0.319 g, 3.3 mmol) in pyridine (5 mL) at 0° C. was slowly added cyclohexanesulfonyl chloride (0.500 g, 2.7 mmol). The reaction mixture was warmed to room temperature and stirred for 16 hrs. The mixture was concentrated and the residue was dissolved in ethyl acetate. The organic layer was washed with 1N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-50% ethyl acetate/hexanes) to afford the product (0.325 g, 49%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.40 (dd, 1H, J=1.8, 0.9 Hz), 6.35 (dd, 1H, J=3.3, 2.1 Hz), 6.30 (d, 1H, J=3.0 Hz), 4.43 (m, 1H), 4.32 (d, 2H, J=5.7 Hz), 2.75 (tt, 1H, J=12.0, 3.3 Hz), 2.15-2.05 (m, 2H), 1.95-1.80 (m, 2H), 1.70 (m, 1H), 1.60-1.40 (m, 2H), 1.30-1.10 (m, 3H).

Workup

  1. customat 0° C.
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe organic layer was washed with 1N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride
  5. dry with materialdried (anhydrous sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography (0-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-d4762dee41b24a1997c611c1ce625326
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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