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

HRID 2241994Notes

Reaction equation

HRID 2241994 reaction equation
[Cl:1][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.[N:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][C:26]=2[N:28]2[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]2)[CH:21]=[CH:20][CH:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([CH:31]3[CH2:30][CH2:29][N:28]([C:26]4[CH:25]=[CH:24][CH:23]=[C:22]5[C:27]=4[N:18]=[CH:19][CH:20]=[CH:21]5)[CH2:33][CH2:32]3)[CH2:14][CH2:13]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

4

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 589755035-Chloro-8-(piperazin-1-yl)quinolineHCID 592048421-Quinolin-8-yl-piperidin-4-one

Product 1

HCID 120041675-Chloro-8-{4-[1-(8-quinolinyl)-4-piperidinyl]-1-piperazinyl}quinoline

Procedure

Using the synthetic methods described in previous examples, 5-chloro-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 beige solid; MP. 201-203° C.; MS (ES) m/z (relative intensity) 459 (M+H)+ (100).

Sources & evidence

ORD record
ord-1e438a2398584fe89da07f55ae6d5514
Source dataset
uspto-grants-2010_03
Patent number
US07671056B2

Reaction notes

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