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

HRID 229322

Reaction equation

HRID 229322 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0e4c415c1b414c53872ae1fd550760bd
Source dataset
uspto-grants-2009_07
Patent number
US07563781B2

Linked notes

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