Methyl 1-(4-aminophenyl)cyclopentane-1-carboxylate → HCID 59362913, compound

HRID 1668815Notes

Reaction equation

HRID 1668815 reaction equation
Cl[C:2]1[C:7]2[CH2:8][CH2:9][CH2:10][C:6]=2[N:5]=[C:4]([CH2:11][CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[N:3]=1.[CH3:17][O:18][C:19]([C:21]1([C:26]2[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:20]>C(O)(C)C>[CH3:17][O:18][C:19]([C:21]1([C:26]2[CH:27]=[CH:28][C:29]([NH:32][C:2]3[C:7]4[CH2:8][CH2:9][CH2:10][C:6]=4[N:5]=[C:4]([CH2:11][CH:12]4[CH2:16][CH2:15][CH2:14][CH2:13]4)[N:3]=3)=[CH:30][CH:31]=2)[CH2:22][CH2:23][CH2:24][CH2:25]1)=[O:20]

Participants

4

Reactant 2

HCID 15086389Methyl 1-(4-aminophenyl)cyclopentane-1-carboxylateHCID 59362951HCID 59362951, compound

Product 1

HCID 59362913HCID 59362913, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chloro-2-cyclopentylmethyl-6,7-dihydro-5H-cyclopentapyrimidine (0.38 g, 1.6 mmol) and 1-(4-amino-phenyl)-cyclopentane carboxylic acid methyl ester (0.35 g, 1.6 mmol) in anhydrous isopropanol (8 mL) was heated at reflux under nitrogen for 8 to 18 hours. Thereafter, volatiles were evaporated under reduced pressure. The residue was triturated with ether and filtered. The solid was dissolved in ethyl acetate, washed with 5% sodium bicarbonate, dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure to afford the title compound as a light yellow powder (0.42 g, 63% yield).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 8 to 18 hours
  3. customThereafter, volatiles were evaporated under reduced pressure
  4. customThe residue was triturated with ether
  5. filtrationfiltered
  6. dissolutionThe solid was dissolved in ethyl acetate
  7. washwashed with 5% sodium bicarbonate
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-63adb21169e146ebb5a0836267e83b45
Source dataset
uspto-grants-2011_08
Patent number
US07989463B2

Reaction notes

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