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Butylamine → 2-n-Butylamino-4-(3-diethylamino-1-propoxy)nitrobenzene

HRID 8051
Notes
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Reaction equation

HRID 8051 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]([NH2:24])[CH2:21][CH2:22][CH3:23]>C1COCC1>[CH2:20]([NH:24][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][CH2:22][CH3:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 8007ButylamineHCID 220147332-Fluoro-4-(3-diethylamino-1-propoxy)nitrobenzene

Product 1

HCID 220147322-n-Butylamino-4-(3-diethylamino-1-propoxy)nitrobenzene

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 n-butylamine (2.4 eq) 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-n-butylamino-4-(3-diethylamino-1-propoxy)nitrobenzene (580 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-a53bb23cec524e1b93bdd268e5e66548
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07087632B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes