Dichloromethane → 1-(Benzo-2,1,3-thiadiazole-5-ylcarbonyl)piperidine

HRID 1581509

반응식

HRID 1581509 반응식
ClCCl.[NH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[N:10]1[S:11][N:12]=[C:13]2[CH:18]=[C:17]([C:19](OC)=[O:20])[CH:16]=[CH:15][C:14]=12>C1(C)C=CC=CC=1>[N:10]1[S:11][N:12]=[C:13]2[CH:18]=[C:17]([C:19]([N:4]3[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]3)=[O:20])[CH:16]=[CH:15][C:14]=12

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 8082PiperidineHCID 696381Methyl 2,1,3-benzothiadiazole-5-carboxylate

생성물 1

HCID 158952351-(Benzo-2,1,3-thiadiazole-5-ylcarbonyl)piperidine수율 87%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Trimethylaluninum (2M in toluene; 3.0 mL, 6.0 mmol) was diluted into 30 mL dichloromethane to which piperidine (0.55 g, 6.5 mmol) and methyl benzo-2,1,3-thiadiazole-5-carboxylate (1.16 g, 6.00 mmol) were added. The reaction was stirred at room temperature for 2 hours and concentrated to one-half the volume by rotary evaporation. Dry toluene (25 mL) was added and the reaction solution was heated to 80° C. for 1 hour. Additional piperidine (about 0.2 g) was added and the temperature was increased to 100° C. for 1 hour. The solution was allowed to cool to room temperature and stirred overnight, at which time it was quenched with 10% citric acid and hydrochloric acid. The solution was diluted with ethyl acetate and sequentially washed with 10% citric acid, saturated sodium hydrogen phosphate and saturated sodium chloride, and subsequently dried over anhydrous sodium sulfate. The solution was concentrated onto silica and product was eluted with hexane/ethyl acetate (3:1). Purification by distillation in a kugelrohr at 180° C. and 0.5 mmHg yielded 1-(benzo-2,1,3-thiadiazole-5-ylcarbonyl)piperidine, 1 (1.29 g, 87%) as a pale yellow oil. IR: 2920, 2855, 1633, 1478, 1439, 1280, 1223, 1001, 816, and 748 cm−1. 1H NMR (500 MHz): δ8.06 (1H, d, J=9.1 Hz); 8.02 (1H, s); 7.63 (1H, t, J=9.0 and 1.5 Hz); 3.77 (2H, br s); 3.40 (2H, br s); 1.72 (4H, br s); and 1.57 ppm (2H, br s).

후처리

  1. additionwere added
  2. concentrationconcentrated to one-half the volume
  3. customby rotary evaporation
  4. additionDry toluene (25 mL) was added
  5. temperaturethe reaction solution was heated to 80° C. for 1 hour
  6. additionAdditional piperidine (about 0.2 g) was added
  7. temperaturethe temperature was increased to 100° C. for 1 hour
  8. temperatureto cool to room temperature
  9. stirringstirred overnight, at which time it
  10. customwas quenched with 10% citric acid and hydrochloric acid
  11. additionThe solution was diluted with ethyl acetate
  12. washsequentially washed with 10% citric acid, saturated sodium hydrogen phosphate and saturated sodium chloride
  13. dry with materialsubsequently dried over anhydrous sodium sulfate
  14. concentrationThe solution was concentrated onto silica and product
  15. washwas eluted with hexane/ethyl acetate (3:1)
  16. customPurification
  17. distillationby distillation in a kugelrohr at 180° C.

출처 및 근거

ORD 기록
ord-f5cf5dc7373a4f09b9ebed9c0242874c
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06730677B2

연결된 노트

불러오는 중…