Hydrazine hydrate (1:1) → (r)-{1-[(1-{2-[4-(2-Aminoethyl)phenyl]ethyl}piperidin-4-yl)methyl]-1h-1,2,4-triazol-3-yl}(cyclohexyl)phenylmethanol

HRID 2383375Notes

Reaction equation

HRID 2383375 reaction equation
[CH:1]1([C@@:7]([OH:47])([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:8]2[N:12]=[CH:11][N:10]([CH2:13][CH:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][C:22]4[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][N:30]5C(=O)C6C(=CC=CC=6)C5=O)=[CH:24][CH:23]=4)[CH2:16][CH2:15]3)[N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.NN>C(O)C>[NH2:30][CH2:29][CH2:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][CH2:20][N:17]2[CH2:16][CH2:15][CH:14]([CH2:13][N:10]3[CH:11]=[N:12][C:8]([C@@:7]([CH:41]4[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46]4)([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[OH:47])=[N:9]3)[CH2:19][CH2:18]2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 591459622-[2-(4-{2-[4-({3-[(R)-cyclohexyl(hydroxy)phenylmethyl]-1H-1,2,4-triazol-1-yl}methyl)piperdin-1-yl]ethyl}phenyl)ethyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 59145973(r)-{1-[(1-{2-[4-(2-Aminoethyl)phenyl]ethyl}piperidin-4-yl)methyl]-1h-1,2,4-triazol-3-yl}(cyclohexyl)phenylmethanolYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-[2-(4-{2-[4-({3-[(R)-cyclohexyl(hydroxy)phenylmethyl]-1H-1,2,4-triazol-1-yl}methyl)piperdin-1-yl]ethyl}phenyl)ethyl]-1H-isoindole-1,3(2H)-dione (Preparation 12, 3.4 g, 5.38 mmol) was suspended in ethanol (20 ml) and hydrazine monohydrate (2.61 ml, 53.8 ml) added. After stirring at reflux for 2 hours, the reaction was cooled to room temperature and the precipitate collected by filtration and washed with ethanol (200 ml). The filtrate was concentrated in vacuo to furnish the title compound as a white solid, in 81% yield, 2.57 g.

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationthe precipitate collected by filtration
  3. washwashed with ethanol (200 ml)
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9565deacebac4b18aad7e6ae7f67f0a4
Source dataset
uspto-grants-2012_09
Patent number
US08263623B2

Reaction notes

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