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

HRID 987558

Reaction equation

HRID 987558 reaction equation
[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]

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 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-8c3923273bc745b8ad9a908711f6d9ed
Source dataset
uspto-grants-2003_10
Patent number
US06632820B1

Linked notes

Loading…