Formaldehyde → 3-(4-Isopropylphenyl)-1',4,6,7-tetramethylspiro[benzofuran-2(3H),4'-piperidine]

HRID 1017867

반응식

HRID 1017867 반응식
Cl.[CH:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[C:15]3([CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[O:14][C:13]3[C:21]([CH3:27])=[C:22]([CH3:26])[CH:23]=[C:24]([CH3:25])[C:12]2=3)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].C=O.[C:30]([BH3-])#N.[Na+]>C(#N)C>[CH:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[C:15]3([CH2:16][CH2:17][N:18]([CH3:30])[CH2:19][CH2:20]3)[O:14][C:13]3[C:21]([CH3:27])=[C:22]([CH3:26])[CH:23]=[C:24]([CH3:25])[C:12]2=3)=[CH:7][CH:6]=1)([CH3:4])[CH3:3]

참가 물질

5

반응물 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21961353HCID 21961353, 화합물

생성물 1

HCID 219613123-(4-Isopropylphenyl)-1',4,6,7-tetramethylspiro[benzofuran-2(3H),4'-piperidine]수율 40%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
0 °C

실험 절차

To a suspension of 3-(4-isopropylphenyl)-4,6,7-trimethylspiro[benzofuran-2(3H),4′-piperidine] hydrochloride (389.6 mg, 1.01 mmol) in acetonitrile (5 ml) was added 37% formalin (2.0 ml) and the mixture was cooled to 0° C. Sodium cyanoborohydride (101.8 mg, 1.62 mmol) was added into this mixture and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure and an aqueous saturated solution of sodium hydrogen carbonate was added to the residue. The product was extracted twice with ethyl acetate. The combined extracts were washed with water, dried on magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was subjected to column chromatography (on Chromatorex NHDM1020 (trade name, manufactured by Fuji Silysia Chemical Ltd.); hexane-ethyl acetate 10:1) to obtain 145.0 mg (40% yield) of the title compound. Melting point: 63-64° C. (Petroleum ether).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionan aqueous saturated solution of sodium hydrogen carbonate was added to the residue
  3. extractionThe product was extracted twice with ethyl acetate
  4. washThe combined extracts were washed with water
  5. customdried on magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-bbb6e9ad580f4315a51c8a9ebb991eae
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479536B1

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