Sodium Iodide → methyl 1-(10,11-dihydro5H-dibenzo[a,d][7]annulen-5-yl)-1,2,5,6-tetrahydropyridine-3-carboxylate

HRID 736790

반응식

HRID 736790 반응식
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[CH2:3]1.[CH2:12]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20](Cl)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13]1.[I-].[Na+].C(N(CC)CC)C>O1CCOCC1>[CH:15]1[C:14]2[CH2:13][CH2:12][C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH:20]([N:2]3[CH2:7][CH2:6][CH:5]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[CH2:3]3)[C:19]=2[CH:18]=[CH:17][CH:16]=1

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 145875H-Dibenzo(a,d)cycloheptene, 10,11-dihydro-5-chloro-HCID 201540Norarecoline Hydrochloride

생성물 1

HCID 68816682methyl 1-(10,11-dihydro5H-dibenzo[a,d][7]annulen-5-yl)-1,2,5,6-tetrahydropyridine-3-carboxylate수율 55%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

A mixture of methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride (crude, 150 mmol), 5-chlorodibenzosuberane (41 g, 180 mmol, 1.2 eq), sodium iodide (2.2 g, 15 mmol, 0.1 eq) and triethylamine (63 mL, 450 mmol, 3.0 eq) in dioxane (300 mL) was stirred at 90° C. overnight. The reaction mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over MgSO4, and concentrated. The crude product was passed through a silica gel plug, eluting with CH2Cl2. After concentration, the resulting solid was triturated with ether to yield 27 g (55%) of methyl 1-(10,11-dihydro5H-dibenzo[a,d][7]annulen-5-yl)-1,2,5,6-tetrahydropyridine-3-carboxylate.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. washeluting with CH2Cl2
  7. concentrationAfter concentration
  8. customthe resulting solid was triturated with ether

출처 및 근거

ORD 기록
ord-7faa392ab5ba428d8d9d7037bc35f0ee
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07595327B2

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