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

HRID 229322

反応式

HRID 229322 の反応式
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][CH:10]2[CH2:12][O:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:15][NH:16][CH3:17]>CO.CN(C)C=O>[CH3:15][N:16]([CH3:17])[CH2:12][CH:10]([OH:11])[CH2:9][O:8][C:7]1[CH:13]=[CH:14][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

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2 回HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2-(4-nitrophenoxymethyl)-oxirane (0.1 mol, 19.52 g) in methanol (150 mL) and dimethyl formamide (50 mL) was added a 2 M solution of dimethylamine in methanol (0.2 mol, 100 mL), and the mixture was stirred at rt overnight. The solvent was evaporated, and the residue was dissolved in a mixture of methylene chloride (300 mL) and methanol (30 mL). A portion of 1 N HCl in diethyl ether (150 mL) was added dropwise, and an oil formed. The oil was separated (ethereal layer was decanted), and the oil was dried under vacuum, yielding 1-dimethylamino-3-(4-nitro-phenoxy)-propan-2-ol (16.6 g) as its hydrochloride salt. MS (ES+) m/z: 240.9 (M+H+). The compound was used as such for the next reaction.

後処理

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in a mixture of methylene chloride (300 mL) and methanol (30 mL)
  3. additionA portion of 1 N HCl in diethyl ether (150 mL) was added dropwise
  4. customan oil formed
  5. customThe oil was separated
  6. custom(ethereal layer was decanted)
  7. customthe oil was dried under vacuum

出典と根拠

ORDレコード
ord-0e4c415c1b414c53872ae1fd550760bd
出典データセット
uspto-grants-2009_07
特許番号
US07563781B2

関連ノート

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