Methyl 1-(4-aminophenyl)cyclopentane-1-carboxylate → HCID 59362947, compound

HRID 1668811Notes

Reaction equation

HRID 1668811 reaction equation
Cl[C:2]1[C:7]2[CH2:8][CH2:9][CH2:10][C:6]=2[N:5]=[C:4]([CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[N:3]=1.[CH3:16][O:17][C:18]([C:20]1([C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=2)[CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:19]>C(O)(C)C>[CH3:16][O:17][C:18]([C:20]1([C:25]2[CH:26]=[CH:27][C:28]([NH:31][C:2]3[C:7]4[CH2:8][CH2:9][CH2:10][C:6]=4[N:5]=[C:4]([CH:11]4[CH2:15][CH2:14][CH2:13][CH2:12]4)[N:3]=3)=[CH:29][CH:30]=2)[CH2:21][CH2:22][CH2:23][CH2:24]1)=[O:19]

Participants

4

Reactant 2

HCID 15086389Methyl 1-(4-aminophenyl)cyclopentane-1-carboxylateHCID 59362936HCID 59362936, compound

Product 1

HCID 59362947HCID 59362947, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chloro-2-cyclopentyl-6,7-dihydro-5H-cyclopentapyrimidine (4.2 g, 18.91 mmol) and 1-(4-amino-phenyl)-cyclopentanecarboxylic acid methyl ester (4.2 g, 19.1 mmol) in anhydrous isopropanol (50 mL) was heated at reflux in a nitrogen atmosphere for 8 to 18 hours. Thereafter, volatiles were evaporated under reduced pressure. The mixture was triturated with ether and filtered. The solid was dissolved in ethyl acetate and washed with 5% sodium bicarbonate and brine. The organic phase was dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure to afford the title compound as a light yellow powder (7.1 g, 93.4% yield).

Workup

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

Sources & evidence

ORD record
ord-acc09b0f70d84f1eb8b3d27e63e2808d
Source dataset
uspto-grants-2011_08
Patent number
US07989463B2

Reaction notes

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