Tert-butyl 4-(2-hydroxyethyl)piperazine-1-carboxylate → tert-butyl 4-(2-(1-oxo-3-phenyl-2-(pyridin-3-yl)-1H-inden-6-yloxy)ethyl)piperazine-1-carboxylate

HRID 331292Notes

Reaction equation

HRID 331292 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:7]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)[C:8]2=[O:11])=[CH:4][CH:3]=1.BrC1C(=O)C2C(C=1C1C=CC=CC=1)=CC=C(O)C=2.O[CH2:43][CH2:44][N:45]1[CH2:50][CH2:49][N:48]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:47][CH2:46]1>>[O:11]=[C:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([O:1][CH2:43][CH2:44][N:45]3[CH2:50][CH2:49][N:48]([C:51]([O:53][C:54]([CH3:55])([CH3:57])[CH3:56])=[O:52])[CH2:47][CH2:46]3)[CH:10]=2)[C:6]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[C:7]1[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 3

HCID 735736Tert-butyl 4-(2-hydroxyethyl)piperazine-1-carboxylateHCID 703061762-bromo-6-hydroxy-3-phenyl-1H-inden-1-oneHCID 703131906-Hydroxy-3-phenyl-2-(pyridin-3-yl)-1H-inden-1-one

Product 1

HCID 70312805tert-butyl 4-(2-(1-oxo-3-phenyl-2-(pyridin-3-yl)-1H-inden-6-yloxy)ethyl)piperazine-1-carboxylateYield 51%

Procedure

The procedure of Step 6 of Example 1 was repeated except for using 6-hydroxy-3-phenyl-2-(pyridin-3-yl)-1H-inden-1-one obtained in Step 1 as a starting material instead of 2-bromo-6-hydroxy-3-phenyl-1H-inden-1-one, t-butyl 4-(2-hydroxyethyl)piperazine-1-carboxylate instead of 4-(2-hydroxyethyl)morpholine, being stirred for 19 h, and being recrystallized with EtOAc to give the title compound (51%).

Workup

  1. custombeing recrystallized with EtOAc

Sources & evidence

ORD record
ord-3a8ddb213530488286b16ea07c441326
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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