Ethyl Bromide → 3-(Anthracen-9-ylmethyl-ethyl-amino)-propan-1-OL

HRID 13003

반응식

HRID 13003 반응식
Br[CH2:2][CH3:3].[CH:4]1[C:17]2[C:8](=[CH:9][C:10]3[C:15]([C:16]=2[CH2:18][NH:19][CH2:20][CH2:21][CH2:22][OH:23])=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:7]=[CH:6][CH:5]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH:14]1[C:15]2[C:10](=[CH:9][C:8]3[C:17]([C:16]=2[CH2:18][N:19]([CH2:2][CH3:3])[CH2:20][CH2:21][CH2:22][OH:23])=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:11]=[CH:12][CH:13]=1

참가 물질

5

반응물 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 114710953-[(Anthracen-9-ylmethyl)-amino]-propan-1-OL

생성물 1

HCID 116879303-(Anthracen-9-ylmethyl-ethyl-amino)-propan-1-OL수율 82%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
75 °C

실험 절차

Bromoethane (616 mg, 5.65 mmol) was dissolved in anhydrous acetonitrile and was added to the stirring mixture of compound 14a (500 mg, 1.9 mmol) and anhydrous K2CO3 (781 mg, 5.7 mmol). The mixture was then stirred overnight at 75° C. under a N2 atmosphere. After confirmation of the disappearance of 14a by TLC, the solution was concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (20 mL) and washed three times with aqueous sodium carbonate. The organic layer was separated, dried with anhydrous Na2SO4, filtered and concentrated under vacuum. Flash column chromatography of the residue gave 14b as a light yellow oil. Yield 82%; Rf=0.35 (3% MeOH/CHCl3); 1H NMR (CDCl3) δ 8.28 (m, 3H), 7.86 (d, 2H), 7.44 (m, 2H), 7.36 (m, 2H), 4.29 (s, 2H), 3.15 (t, 2H), 2.65 (q, 2H), 2.52 (t, 2H), 1.43 (q, 2H), 1.16 (t, 3H); 13C NMR (CDCl3) δ 131.2, 131.1, 129.3, 129.0, 127.6, 125.8, 124.8, 124.4, 63.4, 52.6, 50.5, 47.7, 28.1, 11.6. HRMS (FAB) m/z calcd. for C20H23NO (M+H)+ 294.1852; found 294.1859.

후처리

  1. concentrationAfter confirmation of the disappearance of 14a by TLC, the solution was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in CH2Cl2 (20 mL)
  3. washwashed three times with aqueous sodium carbonate
  4. customThe organic layer was separated
  5. dry with materialdried with anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-13cde27d90644357aafc71add8c12392
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728041B2

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