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

HRID 13003

反応式

HRID 13003 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
75 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-13cde27d90644357aafc71add8c12392
出典データセット
uspto-grants-2010_06
特許番号
US07728041B2

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