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

HRID 860763

Reaction equation

HRID 860763 reaction equation
[O:1]1[CH2:14][CH:2]1[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.[CH3:15][NH:16][CH3:17]>CO.CN(C=O)C>[OH:1][CH:2]([CH2:14][N:16]([CH3:17])[CH3:15])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][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

4-(2,3-Epoxypropoxy)nitrobenzene (obtained as described in Synthetic Communications, 1994, 24, 833; 4.3 g,) was dissolved in methanol (30 ml) and DMF (10 ml). A solution of dimethylamine in methanol (2M, 17 ml) was added and the mixture was stirred overnight. Volatile material was removed by evaporation and the residue was partitioned between saturated sodium bicarbonate (100 ml) and ethyl acetate (100 ml). The organic layer was separated and washed with saturated sodium chloride (2×100 ml) and dried (MgSO4). Concentration gave the product as an oil that slowly crystallised under high vacuum (4.79 g, 89.9%). NMR (CDCl3): 2.33 (s, 6H), 2.98 (m, 1H), 2.54 (m, 1H), 4.00 (m, 3H), 7.00 (d, 2H), 8.20 (d, 2H); MS (M+H)+: 241.

Workup

  1. customVolatile material was removed by evaporation
  2. customthe residue was partitioned between saturated sodium bicarbonate (100 ml) and ethyl acetate (100 ml)
  3. customThe organic layer was separated
  4. washwashed with saturated sodium chloride (2×100 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationConcentration

Sources & evidence

ORD record
ord-1b5988d156b64a06bc51689a4f0e14cb
Source dataset
uspto-grants-2006_12
Patent number
US07153964B2

Linked notes

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