Acetone → 1-[2-(Tetrahydro-2h-pyranyloxy)ethyl]-4-(5-isoquinolyl)aminopiperidine

HRID 10583

Reaction equation

HRID 10583 reaction equation
Cl.[CH:2]1[C:11]2[C:6](=[C:7]([NH:12][CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][CH2:27][O:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][O:30]1.CC(C)=O>CN(C)C=O>[O:30]1[CH2:31][CH2:32][CH2:33][CH2:34][CH:29]1[O:28][CH2:27][CH2:26][N:16]1[CH2:17][CH2:18][CH:13]([NH:12][C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:6]=2[CH:5]=[CH:4][N:3]=[CH:2]3)[CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 114369885-Isoquinolinamine, N-4-piperidinyl-, hydrochloride

Product 1

HCID 219799201-[2-(Tetrahydro-2h-pyranyloxy)ethyl]-4-(5-isoquinolyl)aminopiperidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of the compound of Example 20 (70 mg) and potassium carbonate (142 mg, Kokusan Chemical) in N,N-dimethylformamide (1.5 ml) was added with 2-(2-bromoethoxy)tetrahydro-2H-pyran (254 μl, Aldrich) and stirred at room temperature for 48 hours. The reaction mixture was added with acetone (10 ml), and insoluble matters were separated by filtration. Then, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=6:1) to obtain the title compound (40 mg).

Workup

  1. customwere separated by filtration
  2. customThen, the solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (chloroform:methanol=6:1)

Sources & evidence

ORD record
ord-89e65fdcf54141689ca1a566dc61bce4
Source dataset
uspto-grants-2006_08
Patent number
US07094789B2

Linked notes

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