Acetic Acid → Piperidine, 1-methyl-4-phenyl-, hydrochloride

HRID 885833노트

반응식

HRID 885833 반응식
[ClH:1].[C:2]1([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:18](C)=O.[Na+].CC(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[ClH:1].[CH3:18][N:11]1[CH2:10][CH2:9][CH:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:13][CH2:12]1

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 825094-Phenylpiperidinium chlorideHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 202390Piperidine, 1-methyl-4-phenyl-, hydrochloride수율 76.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 4-phenyl piperidine hydrochloride (1.23 g, 6.2 mmol), formaldehyde (36.5% in H2O, 0.702 ml, 9.3 mmol), NaBH(OAc)3 (2.63 g, 12.42 mmol) and AcOH (0.71 ml, 12.42 mmol) in DCM (30 ml) was stirred for 24 hours at room temperature. The mixture was then brought to basic conditions with a 5% NaHCO3 solution and extracted twice with DCM. The pooled organic phases were dried over Na2SO4 and evaporated to dryness. The residue was dissolved in DCM and treated with HCl in Et2O observing the precipitation of a white solid. The solid was filtered off through a Buchner funnel to obtain 1 g of 1-methyl-4-phenylpiperidine hydrochloride as a white solid.

후처리

  1. extractionextracted twice with DCM
  2. dry with materialThe pooled organic phases were dried over Na2SO4
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in DCM
  5. additiontreated with HCl in Et2O observing
  6. customthe precipitation of a white solid
  7. filtrationThe solid was filtered off through a Buchner funnel

출처 및 근거

ORD 기록
ord-71d06a0a7ee742258550f2b7f0666f99
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242175B2

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