Sodium triacetoxyborohydride → HCID 12004168, compound

HRID 2241995Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[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+]>>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([N:12]3[CH2:17][CH2:16][N:15]([CH:31]4[CH2:30][CH2:29][N:28]([C:26]5[CH:25]=[CH:24][CH:23]=[C:22]6[C:27]=5[N:18]=[CH:19][CH:20]=[CH:21]6)[CH2:33][CH2:32]4)[CH2:14][CH2:13]3)[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

Reactant 3

HCID 5049666Sodium triacetoxyborohydride

HCID 11075146HCID 11075146, compound

HCID 592048421-Quinolin-8-yl-piperidin-4-one

Product 1

HCID 12004168HCID 12004168, compound

Procedure

Using the synthetic methods described in previous examples, 2-methyl-8-(piperazin-1-yl)quinoline (Oruz, et al., J. Med. Chem. 45:4128 (2002)) 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 light brown semi-solid; MS (ES) m/z (relative intensity) 438 (M+H)+ (100).

Sources & evidence

ORD record: ord-d03ff9a6c8a741e3bbda37afbbb761bd
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07671056B2

Reaction notes

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