Pyridine → HCID 19087661, compound

HRID 1464279Notes

Reaction equation

HRID 1464279 reaction equation
[C:1]1([C:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]([C:23]3[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[CH:28][C:24]=3[C:25]([OH:27])=O)[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:35]1C=CC=CC=1.[OH-].[NH4+]>C(#N)C.O>[C:1]1([C:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]([C:23]3[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[CH:28][C:24]=3[C:25]([NH2:35])=[O:27])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 14923Ammonium HydroxideHCID 19087719HCID 19087719, compound

Product 1

HCID 19087661HCID 19087661, compoundYield 39.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-[N-{4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)butyl}-N-ethoxycarbonylamino]-4-nitrobenzoic acid (1.53 g), N,N'-disuccinimidoyl carbonate (924 mg) and pyridine (285 mg) in dry acetonitrile (20 ml) was stirred for 3 hours at room temperature. Then, to the mixture was added 28% ammonium hydroxide (1.4 ml) on an ice-bath. After 1 hour, the reaction mixture was diluted with water, and extracted with chloroform. The extract was washed with brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel (30 g). Elution with a mixed solvent of chloroform and methanol (50:1 V/V) gave 2-[N-{4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)butyl}-N-ethoxycarbonylamino]-4-nitrobenzamide (600 mg) as caramel.

Workup

  1. waitAfter 1 hour
  2. extractionextracted with chloroform
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (30 g)
  7. washElution with a mixed solvent of chloroform and methanol (50:1 V/V)

Sources & evidence

ORD record
ord-c0dfec1d186b4136a682f6fc4f9efd84
Source dataset
uspto-grants-1994_04
Patent number
US05304560

Reaction notes

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