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

HRID 433922

反応式

HRID 433922 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 1-B, 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 ethyl acetate. The ethyl acetate layer was separated and washed twice with saturated brine, dried over anhydrous sodium sulphate, filtered and evaporated to yield 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.S.: (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 ethyl acetate layer was separated
  4. washwashed twice with saturated brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customto yield an oil that
  9. customslowly crystallised under high vacuum (4.79 g, 89.9%)

出典と根拠

ORDレコード
ord-509b8155b009482dbfc7f082a7050417
出典データセット
uspto-grants-2003_12
特許番号
US06670368B1

関連ノート

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