Triethylamine → 4-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-yl)methoxy)piperidine-1-carbonitrile

HRID 1627320Notes

Reaction equation

HRID 1627320 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[C:15]([CH2:24][O:25][CH:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[N:14][CH:13]=2)([CH3:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8].C[CH2:33][N:34](CC)CC.N#CBr>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:12]2[N:16]([C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[C:15]([CH2:24][O:25][CH:26]3[CH2:27][CH2:28][N:29]([C:33]#[N:34])[CH2:30][CH2:31]3)=[N:14][CH:13]=2)([CH3:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10476Cyanogen BromideHCID 66740756HCID 66740756, compound

Product 1

HCID 866622374-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-yl)methoxy)piperidine-1-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-yl)methoxy)piperidine (prepared above) in anhyd DCM (2 mL) was added Et3N (37 uL, 0.27 mmol), followed by cyanic bromide (20 mg, 0.18 mmol). After stirring overnight, the reaction was diluted with DCM, washed with brine, dried over Na2SO4, and concentrated in vacuo to give 4-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-yl)methoxy)piperidine-1-carbonitrile as a white solid that was used directly for the next step.

Workup

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-31e03d82858540ad99281687ac0d184e
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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