Sodium triacetoxyborohydride → 8-{4-[1-(8-Quinolinyl)-4-piperidinyl]-1-piperazinyl}-5-(trifluoromethyl)-quinoline

HRID 2241998Notes

Reaction equation

HRID 2241998 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2.[N:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][C:29]=2[N:31]2[CH2:36][CH2:35][C:34](=O)[CH2:33][CH2:32]2)[CH:24]=[CH:23][CH:22]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[N:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][C:29]=2[N:31]2[CH2:36][CH2:35][CH:34]([N:16]3[CH2:15][CH2:14][N:13]([C:10]4[CH:11]=[CH:12][C:3]([C:2]([F:1])([F:19])[F:20])=[C:4]5[C:9]=4[N:8]=[CH:7][CH:6]=[CH:5]5)[CH2:18][CH2:17]3)[CH2:33][CH2:32]2)[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 592048421-Quinolin-8-yl-piperidin-4-oneHCID 592048478-(1-Piperazinyl)-5-(trifluoromethyl)quinoline

Product 1

HCID 120041708-{4-[1-(8-Quinolinyl)-4-piperidinyl]-1-piperazinyl}-5-(trifluoromethyl)-quinoline

Procedure

Using the synthetic methods described in previous examples, 5-(trifluoromethyl)-8-(piperazin-1-yl)quinoline (Step 3) 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 white solid; MP. 202-204° C.; MS (ES) m/z (relative intensity) 492 (M+H)+ (100).

Sources & evidence

ORD record
ord-245cc2ac129040f48d4680b339379c5a
Source dataset
uspto-grants-2010_03
Patent number
US07671056B2

Reaction notes

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