HCID 68872593, compound → HCID 86631461, compound

HRID 660030Notes

Reaction equation

HRID 660030 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][N:17]2[C:25]3[C:20](=[CH:21][C:22]([CH2:27][OH:28])=[C:23]([Cl:26])[CH:24]=3)[CH:19]=[CH:18]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1.O=[Mn]=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][N:17]2[C:25]3[C:20](=[CH:21][C:22]([CH:27]=[O:28])=[C:23]([Cl:26])[CH:24]=3)[CH:19]=[CH:18]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 68872593HCID 68872593, compound

Product 1

HCID 86631461HCID 86631461, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-[3-(6-chloro-5-hydroxymethyl-indol-1-yl)-propyl]-piperidine-1-carboxylic acid tert-butyl ester (0.55 g, 1.35 mmol) and MnO2 (0.59 mg, 6.77 mmol) in toluene (10 mL) was heated at 100° C. for 30 min. The mixture was cooled to rt and filtered through diatomaceous earth. The filtrate was concentrated and used without further purification. MS: mass calcd. for C22H29ClN2O3, 404.19; m/z found, 405.4 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to rt
  2. filtrationfiltered through diatomaceous earth
  3. concentrationThe filtrate was concentrated
  4. customused without further purification

Sources & evidence

ORD record
ord-f452c06cba5145a891a02ae0c3dee962
Source dataset
uspto-grants-2011_12
Patent number
US08084466B2

Reaction notes

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