Cyclopentylamine → 4-(2-Bromo-acetyl)-N-cyclopentyl-benzenesulfonamide

HRID 737193Notes

Reaction equation

HRID 737193 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1)=[O:4].C(N(CC)CC)C.[CH:22]1([NH2:27])[CH2:26][CH2:25][CH2:24][CH2:23]1>ClCCl>[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:27][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 8471TriethylamineHCID 27568344-(2-bromoacetyl)benzenesulfonyl Chloride

Product 1

HCID 866164394-(2-Bromo-acetyl)-N-cyclopentyl-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-(2-Bromo-acetyl)-benzenesulfonyl chloride (150 mg, 0.17 mmol) was dissolved in 4 mL of dry dichloromethane. To this solution at 0° C., was added triethylamine (0.03 mL, 0.2 mmol), followed by cyclopentylamine (0.2 mmol, 0.011 g). Reaction mixture was stirred at 0° C. for 15 minutes and then quenched with H2O. The reaction mixture was extracted with H2O. The organic phase was isolated, dried over MgSO4 and evaporated. It was used in the next step without any further purification.

Workup

  1. customReaction mixture
  2. customquenched with H2O
  3. extractionThe reaction mixture was extracted with H2O
  4. customThe organic phase was isolated
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customIt was used in the next step without any further purification

Sources & evidence

ORD record
ord-61fd7bb351d74546ab036ec16a3e0970
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

Loading…