4-Chloroaniline → N-(4-Chlorophenyl)-1-(3-chloropyridin-2-yl)-1,2,3,6-tetrahydropyridine-4-carboxamide

HRID 1246697Notes

Reaction equation

HRID 1246697 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[Cl:9][C:10]1[C:11]([N:16]2[CH2:21][CH:20]=[C:19]([C:22](O)=[O:23])[CH2:18][CH2:17]2)=[N:12][CH:13]=[CH:14][CH:15]=1.Cl.CN(C)CCCN=C=NCC>ClCCl>[Cl:9][C:10]1[C:11]([N:16]2[CH2:17][CH:18]=[C:19]([C:22]([NH:6][C:5]3[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][CH:4]=3)=[O:23])[CH2:20][CH2:21]2)=[N:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 219047271-(3-chloropyridin-2-yl)-1,2,3,6-tetrahydropyridine-4-carboxylic Acid

Product 1

HCID 11268050N-(4-Chlorophenyl)-1-(3-chloropyridin-2-yl)-1,2,3,6-tetrahydropyridine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Chloroaniline (13.2 g, 103 mmol), 3′-chloro-3,6-dihydro-2H-1,2′-bipyridine-4-carboxylic acid (16.49 g, 69.1 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (26.5 g, 1.38 mmol) were combined in dichloromethane (150 mL) and stirred overnight at ambient temperature. The mixture was diluted with dichloromethane (200 mL), washed with water (400 mL), 400 mL brine, dried with sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on silica gel using hexane:ethyl acetate (7:3) to provide the title compound. 1H NMR (500 MHz, CDCl3) δ 8.20 (dd, 1H), 7.70 (dd, 1H), 7.62 (s(br) 1H), 7.54 (d, 2H), 7.30 (d, 2H), 6.92 (dd, 1H), 6.76 (m, 1H), 4.16 (dd, 2H), 3.64 (dd, 2H), 2.66 (m, 2H) MS (ESI) 349 (M+H)+.

Workup

  1. washwashed with water (400 mL), 400 mL brine
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-7eae2b8ebc69479b872e9585b0313d65
Source dataset
uspto-grants-2006_10
Patent number
US07129235B2

Reaction notes

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