Cyclohexylamine → HCID 24319741, compound

HRID 1726506Notes

Reaction equation

HRID 1726506 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([S:12](Cl)(=[O:14])=[O:13])=[CH:4][CH:3]=1.[CH:16]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(N(CC)CC)C>C(Cl)Cl>[CH:16]1([NH:22][S:12]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([CH3:1])=[CH:3][CH:4]=2)(=[O:14])=[O:13])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 8471TriethylamineHCID 28007604-methylnaphthalene-1-sulfonyl Chloride

Product 1

HCID 24319741HCID 24319741, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methyl-naphthalene -1-sulfonyl chloride (2.4 g, 10.0 mnmol) in CH2Cl2 (30 mL), was added cyclohexylamine (1.4 g, 11.0 mmol) and triethylamine (2.8 mL, 20.0 mmol) and the resultant solution was stirred at room temperature overnight. The solution was quenched with water and extracted with CH2Cl2 (3×30 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified by Flash columin chromatography (hexane/ethyl acetate, gradient elution) to give the title compound 40 (2.0 g) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.63 (d, 1H), 8.18 (d, 1H1), 8.10 (d, 1H1), 7.64 (m, 2H), 7.38 (d, 1H), 3.08 (m, 1H), 2.76 (s, 3H), 1.52 (m, 5H), 1.09 (m, 5H); LC/MS m/z 304 (M+H)+.

Workup

  1. customThe solution was quenched with water
  2. extractionextracted with CH2Cl2 (3×30 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by Flash columin chromatography (hexane/ethyl acetate, gradient elution)

Sources & evidence

ORD record
ord-16ed541e387c440c92c2d09c194bf147
Source dataset
uspto-grants-2009_02
Patent number
US07491827B2

Reaction notes

Loading…