Piperidine → HCID 54040499, compound

HRID 2120232Notes

Reaction equation

HRID 2120232 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][C:7](=[O:13])[NH:8]2.[Br:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.N1CCCCC1>C(O)C>[Br:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[C:6]2[C:5]3[C:9](=[CH:10][CH:11]=[CH:12][C:4]=3[CH2:3][CH2:2][OH:1])[NH:8][C:7]2=[O:13])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 707414-BromobenzaldehydeHCID 109430044-(2-Hydroxyethyl)indolin-2-one

Product 1

HCID 54040499HCID 54040499, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (3.0 g, 17 mmol), 4-bromobenzaldehyde (3.1 g, 17 mmol) and piperidine (8.4 mL, 85 mmol) in ethanol (113 mL) was heated at 90° C. for overnight. The reaction mixture was concentrated and the residue was chromatographed on a column of silica gel to give 2.4 g (41%) of 3-(4-bromo-benzylidene)-4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one as a yellow orange solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-86b81b572def4f8c9017e75d2feb88eb
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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