1,2-Dichloroethane → HCID 9794750, compound

HRID 432870Notes

Reaction equation

HRID 432870 reaction equation
[NH:1]1[CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1.O([C:14]([NH:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1)=[O:15])C1C=CC=CC=1.[Cl:23]CCCl>>[ClH:23].[N:20]1[CH:19]=[CH:18][C:17]([NH:16][C:14]([N:1]2[CH2:2][CH:3]=[CH:4][CH2:5][CH2:6]2)=[O:15])=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 111,2-DichloroethaneHCID 127501,2,3,6-TetrahydropyridineHCID 11401617Carbamic acid, 4-pyridinyl-, phenyl ester

Product 1

HCID 9794750HCID 9794750, compound

Procedure

A solution of 1,2,3,6-tetrahydropyridine (0.25 g) and 4-phenoxycarbonylaminopyridine (0.64 g) in 1,2-dichloroethane (5 ml) was heated to 75° C. for 6 hours. Evaporation of the solvent gave a residue, which was chlomatographed on silica gel (50 ml) eluting with 0-5% methanol in dichloromethane, and taken up into a solution of hydrogen chloride in ethyl acetate (4N, 2 ml). Evaporation under reduced pressure and trituration with diisopropyl ether gave 1-(pyridin-4-ylcarbamoyl)-1,2,3,6-tetrahydropyridine hydrochloride (0.43 g).

Workup

  1. customEvaporation of the solvent
  2. customgave a residue, which
  3. washeluting with 0-5% methanol in dichloromethane
  4. customEvaporation under reduced pressure and trituration with diisopropyl ether

Sources & evidence

ORD record
ord-720656efe5ae4bdaa909dc81dcfa9cc9
Source dataset
uspto-grants-2003_12
Patent number
US06664293B2

Reaction notes

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