Cyclohexylamine → HCID 24319741, compound

HRID 561327Notes

Reaction equation

HRID 561327 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 65.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methyl-naphthalene-1-sulfonyl chloride (2.4 g, 10.0 mmol) 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 column 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, 1H), 8.10 (d, 1H), 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 column chromatography (hexane/ethyl acetate, gradient elution)

Sources & evidence

ORD record
ord-07d98882c2e6418a973afefdf44ce107
Source dataset
uspto-grants-2011_11
Patent number
US08063222B2

Reaction notes

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