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

HRID 981055

반응식

HRID 981055 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 200716396-Chloromethyl-N,N-dicyclopentylnicotinamide

시약·촉매·용매 2

HCID 962Water용매2회HCID 6212Chloroform용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a693ee75bc374c9ba8ef06ca95f86424
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04990518

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