Potassium Carbonate → HCID 67263598, compound

HRID 1040741Notes

Reaction equation

HRID 1040741 reaction equation
CO[CH:3]1[C:9]2[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][NH:5][CH2:4]1.Br[CH2:18][CH2:19][O:20][CH3:21].[C:22](=O)([O-])[O-:23].[K+].[K+]>CN(C)C=O>[CH3:22][O:23][C:12]1[C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]2[CH2:3][CH2:4][N:5]([CH2:18][CH2:19][O:20][CH3:21])[CH2:6][CH2:7][C:8]=2[CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 67264471HCID 67264471, compound

Product 1

HCID 67263598HCID 67263598, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methoxy-8-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (3.4 g, 0.015 mol), 1-bromo-2-methoxyethane (2.82 mL, 0.030 mol), and potassium carbonate (6.2 g, 0.045 mol), were added to N,N-dimethylformamide (30 mL), and the reaction was stirred over night at room temperature. The reaction mixture was next partitioned between water and ethyl acetate, and the layers were separated. The aqueous phase was extracted twice with ethyl acetate and the combined organic extracts were dried (MgSO4), filtered, and concentrated. Flash chromatography on SiO2 (MeOH/dichloromethane 0-7%,) gave 7-methoxy-3-(2-methoxy-ethyl)-8-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (2.4 g, 55%). 1H-NMR (CDCl3) δ 7.65 (s, 1H), 6.81 (s, 1H), 3.94 (s, 3H), 3.53 (t, J=5.6 Hz, 2H), 3.37 (s, 3H), 2.97 (m, 2H), 2.90 (m, 2H), 2.72 (m, 6H); LC/MS (ESI+): 281.10 (M+H).

Workup

  1. customThe reaction mixture was next partitioned between water and ethyl acetate
  2. customthe layers were separated
  3. extractionThe aqueous phase was extracted twice with ethyl acetate
  4. dry with materialthe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5f9a3e38e5c241f8802ad77fb21a04cb
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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