Dimethylamine → 1-(Dimethylamino)-3-(4-nitrophenoxy)propan-2-ol

HRID 987558

反応式

HRID 987558 の反応式
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][CH:10]2[O:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:15][NH:16][CH3:17]>CO.CN(C=O)C>[CH3:15][N:16]([CH2:11][CH:10]([OH:12])[CH2:9][O:8][C:7]1[CH:13]=[CH:14][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH3:17]

参加物

5

反応物 2

HCID 674DimethylamineHCID 213272-((4-Nitrophenoxy)methyl)oxirane

生成物 1

HCID 31320441-(Dimethylamino)-3-(4-nitrophenoxy)propan-2-ol

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

1-(4-Nitrophenoxy)-2,3-epoxypropane (Reference Example 19, 4.3 g) was dissolved in methanol (30 ml) and DMF (10 ml). Dimethylamine (2M solution in methanol, 17 ml) was added and the mixture was stirred at ambient temperature overnight. The reaction mixture was evaporated to dryness and the residue was dissolved in saturated sodium bicarbonate solution and EtOAc. The EtOAc layer was separated and washed twice with saturated brine, dried over anhydrous sodium sulphate, filtered and evaporated to give the title product as an oil that slowly crystallised under high vacuum (4.79 g, 89.9%). NMR (CDCl3, 300 MHz): 2.33 (s, 6H), 2.98 (m, 1H), 2.54 (m, 1H), 4.00 (m, 3 H), 7.00 (d, 2H), 8.20 (d, 2H); m/z: (ES+) 241 (MH+).

後処理

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionthe residue was dissolved in saturated sodium bicarbonate solution
  3. customThe EtOAc layer was separated
  4. washwashed twice with saturated brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customevaporated

出典と根拠

ORDレコード
ord-8c3923273bc745b8ad9a908711f6d9ed
出典データセット
uspto-grants-2003_10
特許番号
US06632820B1

関連ノート

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