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

HRID 229322

반응식

HRID 229322 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0e4c415c1b414c53872ae1fd550760bd
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563781B2

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