Hydrochloric Acid → 1-Benzyl-4-(2-benzyloxyphenyl)-4-piperidinol

HRID 238273노트

반응식

HRID 238273 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[Mg]Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl.[OH-].[Na+]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[O:22][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 192201-Benzyl-4-piperidoneHCID 178419625HCID 178419625, 화합물

생성물 1

HCID 118248891-Benzyl-4-(2-benzyloxyphenyl)-4-piperidinol수율 61.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 1-benzyl-4-piperidone (0.5 g, 2.6 mmol) in THF (10 mL) was cooled to −78° C. and 2-(benzyloxy)phenyl magnesium bromide (3.2 mmol) was added. The mixture was stirred for 0.5 hours then allowed to warm to room temperature. Hydrochloric acid (1 N, 10 mL) was added carefully and the mixture stirred for 0.1 hour before adding a solution of aqueous sodium hydroxide (1 N, 30 mL). The products were extracted into ethyl acetate, dried over magnesium sulphate, filtered and the solvent removed by evaporation under vacuum. The residue was purified by flash chromatography on silica eluting with 0-50% ethyl acetate/hexane. The fractions containing the desired product were concentrated under vacuum to give the title compound (0.6 g) as a clear, colourless oil.

후처리

  1. stirringthe mixture stirred for 0.1 hour
  2. extractionThe products were extracted into ethyl acetate
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent removed by evaporation under vacuum
  6. customThe residue was purified by flash chromatography on silica eluting with 0-50% ethyl acetate/hexane
  7. additionThe fractions containing the desired product
  8. concentrationwere concentrated under vacuum

출처 및 근거

ORD 기록
ord-31c37b59aeb44b2cb67d4ad3f71418fd
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642621B2

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