Cyclopentylamine → HCID 2058492, compound

HRID 1487231Notes

Reaction equation

HRID 1487231 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].C(N(CC)CC)C.[CH:21]1([NH2:26])[CH2:25][CH2:24][CH2:23][CH2:22]1>ClCCl>[CH:21]1([NH:26][S:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11])[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chloride

Product 1

HCID 2058492HCID 2058492, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-nitrobenzene-1-sulfonyl chloride (22.1 g, 100 mol) in dichloromethane (500 mL) at 0° C. was added triethylamine (14 g, 138.6 mol) and cyclopentanamine (9 g, 105.9 mmol) in several portions over 10-15 minutes. The reaction mixture was stirred at room temperature for 4 hours, concentrated and purified by silica gel chromatography to afford the product N-cyclopentyl-2-nitrobenzenesulfonamide (23 g, yield 85.2%). 1H NMR (400 MHz, CDCl3) δ ppm 8.16-8.18 (m, 1H), 7.84-7.87 (m, 1H), 7.40-7.78 (m, 2H), 5.25-5.27 (d, 1H, J=7.6 Hz), 3.76-3.81 (m, 1H), 1.79-1.87 (m, 2H), 1.62-1.70 (m, 2H), 1.39-1.58 (m, 4H).

Workup

  1. concentrationconcentrated
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-e6581bb665c1459e9adb9ab0a8d0718c
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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