Water → HCID 12050312, compound

HRID 2230167Notes

Reaction equation

HRID 2230167 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:9]=[C:10]1[N:14]([CH:15]2[CH2:20][CH2:19][N:18]([C:21]3(C#N)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[CH2:17][CH2:16]2)[C:13]2[CH:29]=[CH:30][CH:31]=[CH:32][C:12]=2[NH:11]1.[NH4+].[Cl-].O>C1COCC1>[C:1]1([C:21]2([N:18]3[CH2:19][CH2:20][CH:15]([N:14]4[C:13]5[CH:29]=[CH:30][CH:31]=[CH:32][C:12]=5[NH:11][C:10]4=[O:9])[CH2:16][CH2:17]3)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 12050311HCID 12050311, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 12050312HCID 12050312, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of phenylmagnesium bromide (3M solution in diethyl ether, 0.75 ml, 2.25 mmol) in THF (1 ml) was added a suspension of 1-[4-(2-oxo-2,3-dihydro-1H-1,3-benzimidazol-1-yl)piperidino]-1-cyclohexanecarbonitrile (230 mg, 0.71 mmol) in THF (2 ml) at 0° C. Then the reaction mixture was stirred at room temperature for 18 h. To the reaction mixture was added sat.NH4Cl aq. solution (1 ml) followed by addition of water (5 ml). The white precipitate appeared was collected by filtration, washed faith water and CH2Cl2, and dried to give 75 mg (28.1%) of title compound. The filtrate of CH2Cl2 wash was concentrated to give 171 mg of title compound and the starting material mixture, which was purified by column chromatography (silica gel:30 g, CH2Cl2/MeOH:50/1 to 15/1) to give 60 mg(22.5%) of title compound as white powder.

Workup

  1. additionTo the reaction mixture was added
  2. filtrationThe white precipitate appeared was collected by filtration
  3. washwashed faith water and CH2Cl2
  4. customdried

Sources & evidence

ORD record
ord-fb8038d031ea46a295528e7fa7dc0ee6
Source dataset
uspto-grants-2002_07
Patent number
US06423725B1

Reaction notes

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