Water → HCID 67422789, compound

HRID 2070065Notes

Reaction equation

HRID 2070065 reaction equation
[OH-].[Na+].O.C(OC([N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:17][C:16]=2[O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:11][CH2:10]1)=O)C>C(O)C>[CH2:30]([O:29][C:16]1[CH:17]=[C:18]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:19]=[CH:20][C:15]=1[CH:12]1[CH2:13][CH2:14][NH:9][CH2:10][CH2:11]1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67422374HCID 67422374, compound

Product 1

HCID 67422789HCID 67422789, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 500 ml three-necked flask, 9 g of 4-(2,4-bis(benzyloxy)phenyl)piperidine-1-carboxylic acid ethyl ester are dissolved in 180 ml of ethanol, and then 40 ml of a 5M solution of sodium hydroxide are added. The reaction mixture is brought to reflux for 48 hours. The reaction mixture is poured into 400 ml of water. The solid is filtered off and then chromatographed on silica gel (98/2 dichloromethane/methanol). 3.8 g of 4-(2,4-bis(benzyloxy)phenyl)piperidine are obtained.

Workup

  1. temperatureto reflux for 48 hours
  2. filtrationThe solid is filtered off
  3. customchromatographed on silica gel (98/2 dichloromethane/methanol)

Sources & evidence

ORD record
ord-f6a97be67bc944f5a32c8f5715da61c4
Source dataset
uspto-grants-2012_10
Patent number
US08299259B2

Reaction notes

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