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

HRID 901696Notes

Reaction equation

HRID 901696 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-835e13611fa6493a8ee6be2db72a1e93
Source dataset
uspto-grants-2008_04
Patent number
US07361678B2

Reaction notes

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