Potassium Carbonate → 6-Chloromethyl-N,N-dicyclopentylnicotinamide

HRID 981055

Reaction equation

HRID 981055 reaction equation
O[CH2:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]([N:9]([CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:8])=[CH:5][N:4]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:23].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.O>[Cl:23][CH2:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]([N:9]([CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:8])=[CH:5][N:4]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 24819Phosphorus pentachlorideHCID 200716446-Hydroxymethyl-N,N-dicyclopentylnicotinamide

Product 1

HCID 200716396-Chloromethyl-N,N-dicyclopentylnicotinamide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

To a solution of the title product of Example C (1.44 g, 5 mmol) in chloroform (30 mL), phosphorus pentachloride (1.04, 5 mmol) was added. The contents were immersed in an oil-bath at 70° C. and the temperature raised to reflux. After 18h, the pinkish colored reaction solution was cooled to room temperature. The reaction was diluted with water (75 mL) and solid potassium carbonate (2.2 g) added. The contents were stirred for about 10 min until no more effervescence was observed. More water (100 mL) was added and the reaction solution extracted with methylene chloride. The organic layer was separated, dried (MgSO4) and filtered. After removal of solvent, 1 6 g of the title product was isolated as an off-white solid. The compound was used in Example 1 without any further purification. 1H NMR (CDCl3) 1,2-2.2 (m, 16H), 3.6-3.9 (m, 2H), 4.7 (s, 2H), 7.53 (d,J=8 Hz, 1H), 7.74 (dd,J=3,8 Hz, 1H), and 8.56 ppm (d,J=3 Hz, 1H).

Workup

  1. customThe contents were immersed in an oil-bath at 70° C.
  2. temperaturethe temperature raised
  3. temperatureto reflux
  4. additionadded
  5. extractionthe reaction solution extracted with methylene chloride
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customAfter removal of solvent, 1 6 g of the title product
  10. customwas isolated as an off-white solid
  11. customThe compound was used in Example 1 without any further purification

Sources & evidence

ORD record
ord-a693ee75bc374c9ba8ef06ca95f86424
Source dataset
uspto-grants-1991_02
Patent number
US04990518

Linked notes

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