Benzyl Bromide → 3-(Phenylmethyl)-2-piperidinone

HRID 1612753

반응식

HRID 1612753 반응식
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=[O:7].C([Li])CCC.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[NH4+]>O1CCCC1.O>[C:14]1([CH2:13][CH:3]2[CH2:4][CH2:5][CH2:6][NH:1][C:2]2=[O:7])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

7

반응물 4

HCID 7498Benzyl BromideHCID 126652-PiperidoneHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

생성물 1

HCID 44389953-(Phenylmethyl)-2-piperidinone수율 53.9%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-40 °C

실험 절차

To a stirred solution of 2-piperidone (40 g, 0.404 mol) in tetrahydrofuran (800 ml) at 0° C. was added, over a period of 2 hours, n-butyl lithium (2.5 M in hexane, 356 ml, 0.889 mol). The reaction was cooled to -40° C. and a solution of benzyl bromide (48 ml, 0.404 mol) in tetrahydrofuran (200 ml) was added dropwise over a period of 2 hours. The reaction was allowed to warm slowly to room temperature and stirred for 12 hours. Water (100 ml) and saturated aqueous ammonium chloride (100 ml) were added and the aqueous phase separated and extracted with ethyl acetate (3×100 ml). The combined organic phases were washed with brine (200 ml), dried with sodium sulphate and evaporated in vacuo. The resulting solid was recrystallised from toluene to give the desired product as white needles (41.2 g), m.pt. 120°-123° C. Low resolution mass spectroscopy revealed the mass/charge ratio of the parent molecule ion, M+, to be 190 thereby confirming the molecular of the product to be 190.

후처리

  1. temperatureto warm slowly to room temperature
  2. customthe aqueous phase separated
  3. extractionextracted with ethyl acetate (3×100 ml)
  4. washThe combined organic phases were washed with brine (200 ml)
  5. dry with materialdried with sodium sulphate
  6. customevaporated in vacuo
  7. customThe resulting solid was recrystallised from toluene

출처 및 근거

ORD 기록
ord-cd7327f7984e4c9994003e601f8a031c
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05190958

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