Chloroacetaldehyde → Tert-butyl 4-(thiazol-2-yl)piperidine-1-carboxylate

HRID 253982

반응식

HRID 253982 반응식
[C:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)(=[S:3])[NH2:2].Cl[CH2:18][CH:19]=O>CC(C)=O>[S:3]1[CH:19]=[CH:18][N:2]=[C:1]1[CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1

참가 물질

4

반응물 2

HCID 33Chloroacetaldehyde2회HCID 2735648tert-Butyl 4-carbamothioylpiperidine-1-carboxylate

생성물 1

HCID 58179889Tert-butyl 4-(thiazol-2-yl)piperidine-1-carboxylate

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of tert-butyl 4-thiocarbamoylpiperidine-1-carboxylate (1 g, 4.09 mmol) in acetone (5 mL) was added 2-chloroacetaldehyde (0.32 g, 4.08 mmol). The mixture was heated under reflux for 4 hours. Additional 2-chloroacetaldehyde (0.32 g, 4.08 mmol) was added and heating was continued for another 14 hours. The solvent was removed by evaporation and the crude product was purified by silica gel chromatography to give tert-butyl 4-(thiazol-2-yl)piperidine-1-carboxylate as an oil [530 mg (1.97 mmol); LC-MS=213.1 (M+H); 1H NMR (300 MHz, CDCl3) 7.74 (d, J=3.3 Hz, 1H), 7.26 (d, J=3.3 Hz, 1H), 4.23 (brd, 2H), 3.22 (m, 1H), 2.91 (t, 2H), 2.14 (m, 2H), 1.77 (m, 2H), 1.48 (s, 9H)].

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperatureheating
  4. customThe solvent was removed by evaporation
  5. customthe crude product was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-89ac6dc4724d42c688b61ccf506d6284
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872031B2

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