Dimethylformamide → [3-(4-{4-[4-(Adamantan-1-ylmethoxy)-phenyl]-2-isobutyl-imidazol-1-yl}-phenoxy)-propyl]-diethyl-amine

HRID 2237027Notes

Reaction equation

HRID 2237027 reaction equation
[CH2:1]([N:3]([CH2:17][CH3:18])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1)[CH3:2].C[N:20]([CH:22]=O)C.[CH2:24]([O:31][C:32]1[CH:37]=[CH:36][C:35]([C:38](=O)[CH2:39]Br)=[CH:34][CH:33]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O.CCOCC>[C:25]12([CH2:24][O:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]4[N:20]=[C:22]([CH2:34][CH:35]([CH3:38])[CH3:36])[N:14]([C:11]5[CH:12]=[CH:13][C:8]([O:7][CH2:6][CH2:5][CH2:4][N:3]([CH2:17][CH3:18])[CH2:1][CH3:2])=[CH:9][CH:10]=5)[CH:39]=4)=[CH:34][CH:33]=3)[CH2:30][CH:29]3[CH2:24][CH:25]([CH2:30][CH:27]([CH2:28]3)[CH2:26]1)[CH2:26]2

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 2057886N,N-diethyl-3-(4-nitrophenoxy)propan-1-amineHCID 105425931-[4-(Benzyloxy)phenyl]-2-bromoethan-1-one

Product 1

HCID 59699109[3-(4-{4-[4-(Adamantan-1-ylmethoxy)-phenyl]-2-isobutyl-imidazol-1-yl}-phenoxy)-propyl]-diethyl-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of N,N-diethyl-N-[3-(4-nitrophenoxy)propyl]amine (1.0 eq., 2.5 mmol) in anhydrous DMF (20 mL) DIEA (3 eq) was added, followed by slow addition of the 1-[4-(benzyloxy)phenyl]-2-bromoethanone (2.5 mmol). The reaction mixture was stirred under nitrogen at rt until completion, as indicated by HPLC. The reaction mixture was then diluted with cold H2O and the product was isolated in Et2O. The combined organic layers were washed with brine and dried over sodium sulfate. Evaporation of solvent in vacuuo afforded the desired product. The crude alkylated aniline was purified by chromatography (Silica gel). Pure product was obtained from 2-7% MeOH/DCM (yield ˜30%).

Workup

  1. washThe combined organic layers were washed with brine
  2. dry with materialdried over sodium sulfate
  3. customEvaporation of solvent in vacuuo

Sources & evidence

ORD record
ord-e8ed441a371340989a0e10b8e9a6c712
Source dataset
uspto-grants-2010_05
Patent number
US07714013B2

Reaction notes

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