Propylamine → 2-(Propylamino)-4-(3-diethylamino-1-propoxy)nitrobenzene

HRID 2054540

Reaction equation

HRID 2054540 reaction equation
F[C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[CH:5]=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18].[CH2:20]([NH2:23])[CH2:21][CH3:22]>C1COCC1>[CH2:20]([NH:23][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[CH:5]=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18])[CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 220147332-Fluoro-4-(3-diethylamino-1-propoxy)nitrobenzene

Product 1

HCID 220147142-(Propylamino)-4-(3-diethylamino-1-propoxy)nitrobenzeneYield 87.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-fluoro-4-(3-diethylamino-1-propoxy)nitrobenzene (2 mmol; preparation described in Example 5) in THF (5 mL) is treated with propylamine (3 mmol) at rt. After completion of the reaction, the reaction mixture is concentrated in vacuo. The residue is redissolved in EtOAc (10 mL), washed with saturated sodium bicarbonate solution, water, and brine. The organic phase is then dried over sodium sulfate and the solvent is removed in vacuo to afford the product, 2-(propylamino)-4-(3-diethylamino-1-propoxy)nitrobenzene (540 mg) which was used for further transformation without further purification.

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction mixture is concentrated in vacuo
  3. dissolutionThe residue is redissolved in EtOAc (10 mL)
  4. washwashed with saturated sodium bicarbonate solution, water, and brine
  5. dry with materialThe organic phase is then dried over sodium sulfate
  6. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-29d2991b196f46a9a3b7b99241eac72c
Source dataset
uspto-grants-2008_02
Patent number
US07329684B2

Linked notes

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