Piperidin-4-ol → 1-[4-[(1R,3E)-3-hydroxyimino-1-(2-methylphenyl)-3-(2-methyl-4-pyridinyl)propyl]phenyl]piperidin-4-ol

HRID 1617603Notes

Reaction equation

HRID 1617603 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH2:9]/[C:10](/[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[CH:14]=2)=[N:11]\[OH:12])=[CH:4][CH:3]=1.[OH:27][CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>>[OH:27][CH:28]1[CH2:33][CH2:32][N:31]([C:2]2[CH:7]=[CH:6][C:5]([C@H:8]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH3:26])[CH2:9]/[C:10](/[C:13]3[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[CH:14]=3)=[N:11]\[OH:12])=[CH:4][CH:3]=2)[CH2:30][CH2:29]1

Participants

3

Reactant 2

HCID 79341Piperidin-4-olHCID 136166995(NE)-N-[(3R)-3-(4-bromophenyl)-3-(2-methylphenyl)-1-(2-methyl-4-pyridinyl)propylidene]hydroxylamine

Product 1

HCID 1361669971-[4-[(1R,3E)-3-hydroxyimino-1-(2-methylphenyl)-3-(2-methyl-4-pyridinyl)propyl]phenyl]piperidin-4-ol

Procedure

In analogy to example 39, from (E,R)-3-(4-bromophenyl)-1-(2-methylpyridin-4-yl)-3-o-tolylpropan-1-one oxime (example 142, step 1) and 4-hydroxypiperidine was prepared the title compound as a yellow foam, MS (ESI+): m/z=430.2 ([M+H]+).

Sources & evidence

ORD record
ord-454f2e482db2497c8350496e62ac57e0
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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