Diethyl Ether → {1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methanol

HRID 423543

반응식

HRID 423543 반응식
CCOCC.[OH:6][CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]#[N:15])[CH2:10][CH2:9]1.[OH:16][NH:17][C:18](=N)[CH:19]([CH3:21])[CH3:20]>CCOC(C)=O.[Cl-].[Cl-].[Zn+2]>[CH3:20][CH:19]([C:18]1[N:15]=[C:14]([N:11]2[CH2:12][CH2:13][CH:8]([CH2:7][OH:6])[CH2:9][CH2:10]2)[O:16][N:17]=1)[CH3:21]

참가 물질

6

반응물 3

HCID 3283Diethyl EtherHCID 513582894-(Hydroxymethyl)piperidine-1-carbonitrileHCID 178449908HCID 178449908, 화합물

생성물 1

HCID 57930076{1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methanol수율 438%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 1N ZnCl2 in Et2O (182 mL, 182 mmol) was added to a solution of 4-(hydroxymethyl)-1-piperidinecarbonitrile (21.3 g, 152 mmol) and N-hydroxy-2-methylpropanimidamide (18.6 g, 182 mmol) in EtOAc (50 mL) at ambient temperature. The reaction mixture was left at ambient temperature for 30 min, decanted, and was treated with concentrated HCl (45 mL) and ethanol 20 mL). The mixture was heated at reflux for 2 h. The mixture was evaporated to dryness, and the resulting residue was charged with water and the pH was adjusted to basic with K2CO3. The mixture was extracted with EtOAc and the material obtained was combined with 9 other batches prepared similarly and purified by silica gel chromatography to give 150 g of {1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methanol.

후처리

  1. customdecanted
  2. additionwas treated with concentrated HCl (45 mL) and ethanol 20 mL)
  3. temperatureThe mixture was heated
  4. temperatureat reflux for 2 h
  5. customThe mixture was evaporated to dryness
  6. additionthe resulting residue was charged with water
  7. extractionThe mixture was extracted with EtOAc
  8. customthe material obtained
  9. customprepared similarly
  10. custompurified by silica gel chromatography

출처 및 근거

ORD 기록
ord-132c494bbfdd4826bd3d9099cd03ce51
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101634B2

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