Water → HCID 178462556, compound

HRID 1532351Notes

Reaction equation

HRID 1532351 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=2)[CH:5]=[C:4]1[CH2:14][CH2:15][C@@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[C:21](=[O:29])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:2].Cl.[NH2:31][OH:32].C(=O)([O-])[O-].[Na+].[Na+].O>CO>[OH:32][N:31]=[N:13][CH2:12][C:9]1[CH:10]=[C:11]2[C:6]([CH:5]=[C:4]([CH2:14][CH2:15][C@@H:16]3[CH2:20][CH2:19][CH2:18][N:17]3[C:21](=[O:29])[CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:3]2[CH2:1][CH3:2])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 53926880HCID 53926880, compound

Product 1

HCID 178462556HCID 178462556, compoundYield 5.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

190 mg of 1-ethyl-2-[2-[(S)-1-(2-phenylacetyl)pyrrolidin-2-yl]ethyl]indole-6-carbonitrile obtained in Example 14-a) was dissolved in methanol. 103 mg of hydroxylamine hydrochloride and 210 mg of sodium carbonate were added and the reaction solution was refluxed overnight with stirring. After water was added, the reaction solution was extracted two times with dichloromethane. The extract was dried over MgSO4 and distilled under reduced pressure. The residue was purified with silica gel column chromatography [eluent: dichloromethane/methanol (20:1)] to obtain 11 mg of the title compound.

Workup

  1. temperaturethe reaction solution was refluxed overnight
  2. extractionthe reaction solution was extracted two times with dichloromethane
  3. dry with materialThe extract was dried over MgSO4
  4. distillationdistilled under reduced pressure
  5. customThe residue was purified with silica gel column chromatography [eluent: dichloromethane/methanol (20:1)]

Sources & evidence

ORD record
ord-65290f487b934f399aea644ffdb04302
Source dataset
uspto-grants-2001_03
Patent number
US06201006B1

Reaction notes

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