4-Methylbenzyl chloride → 1-(4-Methylbenzyl)piperidin-4-ol

HRID 277157

반응식

HRID 277157 반응식
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH3:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Cl)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)(C)C>[CH3:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][N:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)=[CH:11][CH:10]=1

참가 물질

5

반응물 3

HCID 77224-Methylbenzyl chlorideHCID 11430Potassium CarbonateHCID 79341Piperidin-4-ol

생성물 1

HCID 7914821-(4-Methylbenzyl)piperidin-4-ol수율 51.6%

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

Synthesis of this compound was accomplished according to Scheme 33. To 5.05 g (50 mmol) of 4-hydroxypiperidine and 7.08 g (50 mmol) of p-methylbenzyl chloride in 25 mL of tert-butanol was added excess solid potassium carbonate, and the mixture was heated on a steam bath for 3 h. The mixture was cooled to room temperature and partitioned between ether and water. The organic phase was extracted with cold dilute HCl, and the acidic aqueous phase was extracted with ether twice. The aqueous phase was made basic with ice and 50% aqueous NaOH and extracted with ether. The ether phase was washed with dilute aqueous sodium bicarbonate solution, brine, dried, and evaporated under vacuum to give 5.3 g (52) of 1-(4-methylbenzyl)-4-hydroxypiperidine (123) as an oil. GC/MS showed 100% purity with a molecular ion of 205.

후처리

  1. customSynthesis of this compound
  2. temperaturethe mixture was heated on a steam bath for 3 h
  3. custompartitioned between ether and water
  4. extractionThe organic phase was extracted with cold dilute HCl
  5. extractionthe acidic aqueous phase was extracted with ether twice
  6. extractionextracted with ether
  7. washThe ether phase was washed with dilute aqueous sodium bicarbonate solution, brine
  8. customdried
  9. customevaporated under vacuum

출처 및 근거

ORD 기록
ord-40bf85493a0040dfb069d802b5653eb2
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06355660B1

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