Ethanol → HCID 178504662, compound

HRID 1622230Notes

Reaction equation

HRID 1622230 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[C:13]3[CH2:19][CH:18]([CH:20]4[CH2:25][CH2:24][N:23]([C:26]#[N:27])[CH2:22][CH2:21]4)[O:17][C:14]3=[CH:15][N:16]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Cl.[NH2:29][OH:30].C(=O)([O-])[O-].[K+].[K+].C(O)C>O>[OH:30][NH:29][C:26]([N:23]1[CH2:24][CH2:25][CH:20]([CH:18]2[O:17][C:14]3=[CH:15][N:16]=[C:11]([C:8]4[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=4)[CH:12]=[C:13]3[CH2:19]2)[CH2:21][CH2:22]1)=[NH:27]

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 86675674HCID 86675674, compound

Product 1

HCID 178504662HCID 178504662, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-[5-(4-methanesulfonyl-phenyl)-2,3-dihydro-furo[2,3-c]pyridin-2-yl]-piperidine-1-carbonitrile (175 mg), hydroxylamine hydrochloride (50 mg), potassium carbonate (70 mg), ethanol (1 mL), and water (1.5 mL) is heated under reflux for 2 h. The reaction mixture is concentrated in vacuo and chromatographed on silica gel (dichloromethane/methanol 92:8→60:40) to give the title compound. LC (method 5): tR=0.65 min; Mass spectrum (ESI+): m/z=417 [M+H]+.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 2 h
  3. concentrationThe reaction mixture is concentrated in vacuo
  4. customchromatographed on silica gel (dichloromethane/methanol 92:8→60:40)

Sources & evidence

ORD record
ord-305739c4d9c743f49bc7b8506cdff8bd
Source dataset
uspto-grants-2014_07
Patent number
US08778926B2

Reaction notes

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