3-Cyclohexene-1-carbonyl chloride → HCID 57004125, compound

HRID 963259

Reaction equation

HRID 963259 reaction equation
[CH3:1][C@@H:2]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[CH2:3][N:4]1[CH2:9][CH:8]=[C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5]1.[CH:22]1([C:28](Cl)=[O:29])[CH2:27][CH2:26][CH:25]=[CH:24][CH2:23]1>C(Cl)Cl>[CH3:1][C@@H:2]([N:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[C:28]([CH:22]1[CH2:27][CH2:26][CH:25]=[CH:24][CH2:23]1)=[O:29])[CH2:3][N:4]1[CH2:5][CH:6]=[C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 5230583-Cyclohexene-1-carbonyl chlorideHCID 18660712(R)-[1-Methyl-2-(4-thiophen-2-yl-1,2,3,6-tetrahydropyrid-1-yl)ethyl]-pyrid-2-yl-amine

Product 1

HCID 57004125HCID 57004125, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the starting (R)-[1-methyl-2-(4-thiophen-2-yl-3,6-dihydro-2H-pyrid-1-yl)-ethyl]-pyrid-2-yl-amine (0.46 g, 1.5 mmol) in methylene chloride (20 ml) was cooled to 0° C., after which a solution of cyclohex-3-enecarbonyl chloride (0.222 g, 1.5 mmol) in methylene chloride (10 ml) was dropwise added under exclusion of moisture. The reaction mixture was stirred at ambient temperature overnight, then washed with 2.5N NaOH (10 ml). The separated organic layer was washed with brine (50 ml), dried over magnesium sulfate, filtered, and evaporated to dryness in vacuo. Column chromatography on 50 g of silica gel with chloroform as eluant, followed by trituration in ether with the addition of ethanolic HCl gave 0.27g of the title compound as the dihydrochloride, m.p. 92°-6° C.

Workup

  1. washwashed with 2.5N NaOH (10 ml)
  2. washThe separated organic layer was washed with brine (50 ml)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness in vacuo
  6. additionColumn chromatography on 50 g of silica gel with chloroform as eluant, followed by trituration in ether with the addition of ethanolic HCl

Sources & evidence

ORD record
ord-e997d55740634178bf491cfc3d1247a7
Source dataset
uspto-grants-1998_06
Patent number
US05763460

Linked notes

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