O-Phenylenediamine → N-[1-(1,2,2a,3,4,5-hexahydroacenaphthylen-1-yl)piperidin-4-yl]-benzene-1,2-diamine

HRID 331227노트

반응식

HRID 331227 반응식
[CH:1]1([N:13]2[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][CH:3]3[CH2:2]1.[C:20]1([NH2:27])[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH2:26].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>ClC(Cl)C.O.C(O)(=O)C>[CH:1]1([N:13]2[CH2:18][CH2:17][CH:16]([NH:26][C:21]3[C:20]([NH2:27])=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:15][CH2:14]2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][CH:3]3[CH2:2]1

참가 물질

8

반응물 4

HCID 7243O-PhenylenediamineHCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 687066711-(1,2,2a,3,4,5-Hexahydroacenaphthylen-1-yl)piperidin-4-one

생성물 1

HCID 68704972N-[1-(1,2,2a,3,4,5-hexahydroacenaphthylen-1-yl)piperidin-4-yl]-benzene-1,2-diamine수율 85.2%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 63651,1-Dichloroethane용매

실험 절차

To a cooled (0° C.) solution of 1-(1,2,2a,3,4,5-hexahydroacenaphthylen-1-yl)piperidin-4-one (1.00 g, 3.92 mmol) and 1,2-phenylenediamine (642 mg) in dichloroethane (30 ml) were added sodium triacetoxyborohydride (1.99 g) and acetic acid (0.509 ml), and the mixture was stirred at room temperature for 19 hr. The reaction mixture was poured into water, and the mixture was neutralized with potassium carbonate, and extracted with chloroform. The extract was washed with water and saturated brine, dried over sodium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (chloroform/methanol) to give N-[1-(1,2,2a,3,4,5-hexahydroacenaphthylen-1-yl)piperidin-4-yl]-benzene-1,2-diamine (1.16 g) as an oil.

후처리

  1. extractionextracted with chloroform
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol)

출처 및 근거

ORD 기록
ord-c4558bebad384ff8a7c6d7786f699d6c
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877779B2

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