Cyclopentylamine → HCID 10513814, compound

HRID 1940492Notes

Reaction equation

HRID 1940492 reaction equation
[CH2:1]([O:8][C:9](=[O:12])[CH2:10]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCl.[CH:15]1([NH2:20])[CH2:19][CH2:18][CH2:17][CH2:16]1>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:12])[CH2:10][NH:20][CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 24526ChlorineHCID 62576Benzyl bromoacetate2×

Product 1

HCID 10513814HCID 10513814, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of Benzyl-2-bromoacetate (3.30 ml, 20.0 mmol) in 20 mL CH2 Cl2 was added drop-wise to a solution of cyclopentylamine (8.60 g, 100 mmol) in 20 mL of CH2Cl2, with stirring at 0° C. On completion of the addition of benzyl-2-bromoacetate, the reaction was stirred at room temperature 17 hours. The organic solvent was removed in vacuo and the residue was taken up in ethyl acetate and washed with saturated Na2CO3 solution. The solution was extracted with 1N HCl . The aqueous layer was made basic with Na2CO3 and extracted with chloroform. The organic layer was dried (MgSO4) and evaporated. The residue was purified by silica gel flash column chromatography, eluting sequentially with hexane and hexane/ethyl acetate (1:1, v/v) to yield 2.3 g (50.0%) of the title compound as an oil. 1 H NMR (CDCl3) δ 6 1.25-1.85 (m, 9H); 3.0-3.12 (m, 1H); 3.43 (s, 2H); 5.15 (s, 2H); 7.27-7.42 (m, 5H); 13C NMR (CDCl3) δ 23.72, 32.71, 49.53, 59.03, 66.24, 128.1, 128.32, 135.42, 172.29.

Workup

  1. stirringthe reaction was stirred at room temperature 17 hours
  2. customThe organic solvent was removed in vacuo
  3. washwashed with saturated Na2CO3 solution
  4. extractionThe solution was extracted with 1N HCl
  5. extractionextracted with chloroform
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customevaporated
  8. customThe residue was purified by silica gel flash column chromatography
  9. washeluting sequentially with hexane and hexane/ethyl acetate (1:1

Sources & evidence

ORD record
ord-bd078327090548feb178d682b40d970b
Source dataset
uspto-grants-1997_12
Patent number
US05700779

Reaction notes

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