Cyclopentylamine → HCID 59529889, compound

HRID 1410200Notes

Reaction equation

HRID 1410200 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH:15]1([NH2:20])[CH2:19][CH2:18][CH2:17][CH2:16]1>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4]([NH:20][CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:5].[Cl:1][C:2]1[CH:10]=[C:9]([NH:20][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4]([NH:20][CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:5]

Participants

5

Reactant 2

HCID 2906CyclopentylamineHCID 151243842-Chloro-4-fluoro-5-nitrobenzoyl chloride

Product 2

HCID 59529883HCID 59529883, compoundYield 14%HCID 59529889HCID 59529889, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Chloro-4-fluoro-5-nitrobenzoyl chloride (1.5 g, 6.30 mmol) was added to a mixture of cyclopentylamine (430 L, 12.6 mmol), TEA (1.76 mL, 12.6 mmol) and DCM (30 mL) at −20° C. After 12 h at rt, the mixture was diluted with DCM and washed with NH4OH (aq sat). The organic layer was washed with H2O and brine, dried over Na2SO4, concentrated and purified by HPLC to afford 510 mg (28%) of 2-chloro-N-cyclopentyl-4-fluoro-5-nitrobenzamide and 300 mg (14%) of 2-chloro-N-cyclopentyl-4-cyclopentylamino-5-nitrobenzamide.

Workup

  1. washwashed with NH4OH (aq sat)
  2. washThe organic layer was washed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by HPLC

Sources & evidence

ORD record
ord-f107d1112321476db28b0856c6c8b377
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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