Sodium triacetoxyborohydride → 5-Fluoro-8-{4-[4-(8-quinolinyl)-1-piperazinyl]-1-piperidinyl]quinoline

HRID 2241970Notes

Reaction equation

HRID 2241970 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[N:19]1([C:25]2[CH:26]=[CH:27][CH:28]=[C:29]3[C:34]=2[N:33]=[CH:32][CH:31]=[CH:30]3)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[F:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][CH:15]([N:22]3[CH2:23][CH2:24][N:19]([C:25]4[CH:26]=[CH:27][CH:28]=[C:29]5[C:34]=4[N:33]=[CH:32][CH:31]=[CH:30]5)[CH2:20][CH2:21]3)[CH2:14][CH2:13]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 118307868-(1-piperazinyl)QuinolineHCID 592048481-(5-Fluoroquinolin-8-yl)piperidin-4-one

Product 1

HCID 120041965-Fluoro-8-{4-[4-(8-quinolinyl)-1-piperazinyl]-1-piperidinyl]quinolineYield 138.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 0.120 g of 1-(5-fluoro-quinolin-8-yl)-piperidin-4-one (Step 3, 0.22 g) and 8-piperazin-1-ylquinoline (Oruz, et al., J. Med. Chem. 45:4128 (2002), 0.19 g) was added of 0.19 g sodium triacetoxyborohydride and 0.1 mL acetic acid. The reaction was stirred at room temperature overnight. It was quenched with 1N NaOH, and the product was extracted with CH2Cl2. The organic phase was washed with water and dried over magnesium sulfate. The product was filtered through 75 ml of silica gel using 100% Ethyl acetate, to give 0.30 g of the desired product. Mp: 224° C.; MS (ES) m/z (relative intensity): 442 (M++−H, 100).

Workup

  1. customIt was quenched with 1N NaOH
  2. extractionthe product was extracted with CH2Cl2
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe product was filtered through 75 ml of silica gel using 100% Ethyl acetate

Sources & evidence

ORD record
ord-4ef313efd6094420b4278fbfa58941dc
Source dataset
uspto-grants-2010_03
Patent number
US07671056B2

Reaction notes

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