Methanesulfonyl chloride → N-(1-methylcyclopentyl)methanesulfonamide

HRID 1776245Notes

Reaction equation

HRID 1776245 reaction equation
Cl.[NH2:2][C:3]1([CH3:8])[CH2:7][CH2:6][CH2:5][CH2:4]1.[CH3:9][S:10](Cl)(=[O:12])=[O:11]>N1C=CC=CC=1>[CH3:8][C:3]1([NH:2][S:10]([CH3:9])(=[O:12])=[O:11])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 115064601-methylcyclopentan-1-amine Hydrochloride

Product 1

HCID 61688020N-(1-methylcyclopentyl)methanesulfonamideYield 47%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 1-amino-1-methylcyclopentane hydrochloride (0.165 g, 1.2 mmol) in pyridine (1 mL) was added methanesulfonyl chloride (0.169 mL, 2.2 mmol). The reaction mixture was stirred at room temperature for 16 hrs and then concentrated. The mixture was diluted with ethyl acetate and washed with 1 N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), filtered, and concentrated to afford the product as a brown oil (0.100 g, 46%). 1H NMR (300 MHz, CDCl3) δ 4.27 (br s, 1H), 3.04 (s, 3H), 2.00-1.60 (m, 8H), 1.50 (s, 3H).

Workup

  1. concentrationconcentrated
  2. additionThe mixture was diluted with ethyl acetate
  3. washwashed with 1 N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride
  4. dry with materialdried (anhydrous sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c4076586a76b457d90c56cf41281893a
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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