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

HRID 2109629노트

반응식

HRID 2109629 반응식
[C:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.[BH3-][C:16]#N.[Na+].CC(O)=O>CC#N.O.C(Cl)Cl>[CH3:16][N:10]1[CH2:9][CH2:8][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][CH2:11]1

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 698734-PhenylpiperidineHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 202391Piperidine, 1-methyl-4-phenyl-

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

To a stirring mixture at ambient temperature of 4-phenylpiperidine (5.24 g, 32.48 mmol, Step A) in CH3CN (95 ml) was added a 37% solution of HCHO in H2O (13 ml). To this mixture was added NaCNBH3 (3.27 g, 51.97 mmol). AcOH was added dropwise every 10 min over the next h to maintain the reaction pH near 7. The reaction volume was then reduced in vacuo. The reaction mix was diluted with CH2Cl2 and washed with 2N NaOH and then brine. The crude was concentrated in vacuo and eluted through a silica gel column with 10% MeOH/CH2Cl2. The 1-methyl-4-phenylpiperidine was concentrated in vacuo, yielding a clear oil.

후처리

  1. temperatureto maintain
  2. customthe reaction pH near 7
  3. additionThe reaction mix
  4. washwashed with 2N NaOH
  5. concentrationThe crude was concentrated in vacuo
  6. washeluted through a silica gel column with 10% MeOH/CH2Cl2
  7. concentrationThe 1-methyl-4-phenylpiperidine was concentrated in vacuo
  8. customyielding a clear oil

출처 및 근거

ORD 기록
ord-4a9b0b5fccdd4e0b8d048be0540f0fbf
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07514564B2

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