Cyclopentanone → 3-Butyl-6-(cyclopentylamino)-phthalide

HRID 2120184Notes

Reaction equation

HRID 2120184 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([CH2:12][CH2:13][CH2:14][CH3:15])[O:7][C:8]2=[O:9])=[CH:4][CH:3]=1.[C:16]1(=O)[CH2:20][CH2:19][CH2:18][CH2:17]1>C(O)C.[Pd]>[CH2:12]([CH:6]1[C:5]2[C:10](=[CH:11][C:2]([NH:1][CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:3][CH:4]=2)[C:8](=[O:9])[O:7]1)[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 2

HCID 8452CyclopentanoneHCID 98777066-Amino-3-butyl-phthalide

Product 1

HCID 234391113-Butyl-6-(cyclopentylamino)-phthalide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Analogously to the method described in Example 14, 4.1 g (20.0 mmol) of compound obtained in Example 4 in 5 ml of cyclopentanone and 150 ml of 95% ethanol are added to 10% Pd—C catalyst and hydrogenated to give the title compound.

Sources & evidence

ORD record
ord-174719332b204109bb143e6e2ab54ede
Source dataset
uspto-grants-2004_02
Patent number
US06689808B2

Reaction notes

Loading…