1,2,3,6-Tetrahydropyridine → HCID 21918743, compound

HRID 1356434Notes

Reaction equation

HRID 1356434 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH:13]1[CH2:18][CH:17]=[CH:16][CH2:15][CH2:14]1>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]([N:13]2[CH2:18][CH2:17][CH:16]=[CH:15][CH2:14]2)=[O:12])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 127501,2,3,6-TetrahydropyridineHCID 66012Benzene, 1-isocyanato-4-nitro-

Product 1

HCID 21918743HCID 21918743, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

900 mg (5 mmol) of 4-nitrophenylisocyanate is dissolved, under an argon atmosphere, in a 100 ml three-necked flask in 17 ml of dry DMF. 0.45 ml (5 mmol) of 1,2,3,6-tetrahydropyridine is added to this solution in one go, and agitation is maintained for 15 hours. The reaction mixture is then concentrated to dryness under vacuum and the evaporation residue placed on a silica gel column. After elution with a heptane/ethyl acetate mixture: 4/6, the pure fractions are collected and concentrated under reduced pressure in order to produce 860 mg (70%) of a bright yellow powder. Melting point: 169-170° C.

Workup

  1. temperatureis maintained for 15 hours
  2. concentrationThe reaction mixture is then concentrated to dryness under vacuum
  3. washAfter elution with a heptane/ethyl acetate mixture
  4. custom4/6, the pure fractions are collected
  5. concentrationconcentrated under reduced pressure in order

Sources & evidence

ORD record
ord-723cfea87b5848f49c6f5d4228e8f5e3
Source dataset
uspto-grants-2003_07
Patent number
US06586454B2

Reaction notes

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