1-Chloro-4-piperidino-2-naphthol → 4-Piperidino-2-naphthol

HRID 54598

반응식

HRID 54598 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:4][C:3]=1[OH:18]>[OH-].[Na+].[Ni]>[N:12]1([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:2]=[C:3]([OH:18])[CH:4]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

참가 물질

4

반응물 1

HCID 199595221-Chloro-4-piperidino-2-naphthol

생성물 1

HCID 199595274-Piperidino-2-naphthol수율 56%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 14798Sodium Hydroxide용매

실험 절차

1-Chloro-4-piperidino-2-naphthol (3.0 g;0.0115 mol), prepared as in 1(a) above, dissolved in 1.25M aqueous NaOH (100 ml) was stirred and heated to 75°-80° C. To the solution was added (50/50) Raney Nickel (14.0 g) portionwise over 1 hour. The mixture was stirred for 1.5 h, cooled then filtered through celite with washing (3×2M NaOH). The filtrate was neutralised with conc. HCl and extracted into CH2Cl2, dried and evaporated to yield crude 4-piperidino-2-naphthol (1.46 g;56%) as a red-orange oil. Purification by flash chromatography over silica (CH2Cl2) gave 4-piperidino-2-naphthol (of structure 4a below) as a red oil. ##STR16## (c) A mixture of 4-piperidino-2-naphthol (1.00 g; 0.0044 mol) , prepared as described in 1(b) above, 1,1-dianisylprop-2-yn-1-ol(1.18 g;0.0044 mol), acidic alumina Brockmann 1 (4 g) and toluene (40.0 ml) was heated and stirred for 1.5 h, cooled and filtered. The filtrate was washed with 2M NaOH then water, dried and evaporated to give a red gum. Purification of the gum by flash chromatography over silica (20% ethylacetate in hexane) affored an orange gum which upon trituration with pet. ether (40-60)/diethyl ether yielded 3,3-dianisyl-6-piperidino -3H-naphtho[2,1-b]pyran (of structure 5a below) as an off-white solid (5% yield), m.pt. 114°-119° C. ##STR17##

후처리

  1. temperatureheated to 75°-80° C
  2. stirringThe mixture was stirred for 1.5 h
  3. temperaturecooled
  4. filtrationthen filtered through celite
  5. washwith washing (3×2M NaOH)
  6. extractionextracted into CH2Cl2
  7. customdried
  8. customevaporated

출처 및 근거

ORD 기록
ord-9f5902cfa37444f4bd13faebf29e7ee0
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05623005

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