Aniline → HCID 11385426, compound

HRID 1026688Notes

Reaction equation

HRID 1026688 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]3=[O:24])=[CH:10][C:9]=2[F:25])[CH2:4][CH2:3]1.[C-:26]#[N:27].[Na+].[NH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(O)(=O)C>[C:30]1([NH:29][C:2]2([C:26]#[N:27])[CH2:3][CH2:4][N:5]([C:8]3[CH:13]=[CH:12][C:11]([N:14]4[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]4=[O:24])=[CH:10][C:9]=3[F:25])[CH2:6][CH2:7]2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 8929Sodium CyanideHCID 54375226N-[(5S)-3-[3-fluoro-4-(4-oxopiperidinyl)phenyl]-2-oxo-5-oxazolidinyl]methylacetamide

Product 1

HCID 11385426HCID 11385426, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of (S)—N-{3-[4-(4-oxo-piperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (0.57 mmol), sodium cyanide in 5 ml acetic acid was stirred at room temperature for 1 hour. To the reaction mixture aniline was added and was stirred at 60° C. for overnight. The solvent was removed in vacuum and the residue was extracted with chloroform and was washed with water and dried. Evaporation of solvent followed by silica gel chromatographic purification afforded the title compound in 51% yield. M.P. 81-85° C. and MS (M+1)=452 (MH+, 100%) for M.F.=C24H26FN5O3.

Workup

  1. stirringwas stirred at 60° C. for overnight
  2. customThe solvent was removed in vacuum
  3. extractionthe residue was extracted with chloroform
  4. washwas washed with water
  5. customdried
  6. customEvaporation of solvent
  7. customfollowed by silica gel chromatographic purification

Sources & evidence

ORD record
ord-33f4c03103d74ff097217d2fc255a6d9
Source dataset
uspto-grants-2014_05
Patent number
US08729269B2

Reaction notes

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