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

HRID 2242000Notes

Reaction equation

HRID 2242000 reaction equation
F[C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[F:18][C:19]1[CH:28]=[CH:27][C:26](O)=[C:25]2[C:20]=1[CH:21]=[CH:22][CH:23]=[N:24]2.[N:30]1[C:39]2[C:34](=CC=CC=2N2CCC(=O)CC2)[CH:33]=[CH:32][CH:31]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[F:18][C:19]1[CH:28]=[CH:27][C:26]([N:30]2[CH2:39][CH2:34][CH:33]([N:15]3[CH2:16][CH2:17][N:12]([C:9]4[CH:10]=[CH:11][CH:2]=[C:3]5[C:8]=4[N:7]=[CH:6][CH:5]=[CH:4]5)[CH2:13][CH2:14]3)[CH2:32][CH2:31]2)=[C:25]2[C:20]=1[CH:21]=[CH:22][CH:23]=[N:24]2

Participants

5

Reactant 4

HCID 2179075-Fluoro-8-quinolinolHCID 5049666Sodium triacetoxyborohydrideHCID 592048421-Quinolin-8-yl-piperidin-4-oneHCID 592048735-Fluoro 8-(piperazin-1-yl)quinoline

Product 1

HCID 120041965-Fluoro-8-{4-[4-(8-quinolinyl)-1-piperazinyl]-1-piperidinyl]quinoline

Procedure

Using the synthetic methods described in previous examples, 5-fluoro 8-(piperazin-1-yl)quinoline (Prepared from commercially available 5-fluoro-8-hydroxyquinoline using the methodology described for Example R, step 3, above) and 1-quinolin-8-yl-piperidin-4-one (Example A, Step 5, above) were reacted with sodium triacetoxyborohydride to give the desired product as a yellow solid; MP. 222-224° C.; MS (ES) m/z (relative intensity) 442 (M+H)+ (100).

Sources & evidence

ORD record
ord-dbe8f97cb8ba4c2a93dae14ca5919e1f
Source dataset
uspto-grants-2010_03
Patent number
US07671056B2

Reaction notes

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