Cyclopentylamine → HCID 59540382, compound

HRID 923389Notes

Reaction equation

HRID 923389 reaction equation
[CH:1]1([NH2:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1>CN(C)C=O.O>[N+:21]([C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:6]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:16][CH:17]=1)([O-:23])=[O:22]

Participants

6

Reactant 3

HCID 2906CyclopentylamineHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromide2×

Product 1

HCID 59540382HCID 59540382, compoundYield 103.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of cyclopentylamine (0.148 mL, 1.5 mmol) in N,N-dimethylformamide (2 mL) was added potassium carbonate (622 mg, 4.50 mmol) followed by 1-(bromomethyl)-4-nitrobenzene (648 mg, 3.00 mmol). The resulting mixture was stirred at rt for 16 hours, more 1-(bromomethyl)-4-nitrobenzene was added (324 mg, 1.5 mmol), and stirring was continued for an additional 2 hours. The mixture was diluted with water, extracted with CH2Cl2, and the organic layer was dried (Na2SO4), filtered and concentrated. The crude product was purified by precipitation from methanol to afford the title compound (554 mg, quant.). MS (ESI) m/z 356.0 (M+H)+.

Workup

  1. stirringstirring
  2. waitwas continued for an additional 2 hours
  3. extractionextracted with CH2Cl2
  4. dry with materialthe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by precipitation from methanol

Sources & evidence

ORD record
ord-de7f4410c3cd4f0ab5e91c7c3cd5f9c6
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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