Dimethylformamide → HCID 12811315, compound

HRID 543495Notes

Reaction equation

HRID 543495 reaction equation
[OH:1][CH:2]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1)[CH:3]([N:5]1[CH2:10][CH2:9][CH:8]([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[NH:13][C:12]2=[O:20])[CH2:7][CH2:6]1)[CH3:4].C(N([CH2:36][CH3:37])CC)C.CN(C)C=[O:41]>CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[OH:1][CH:2]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1)[CH:3]([N:5]1[CH2:10][CH2:9][CH:8]([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]([C:36](=[O:41])[CH3:37])[C:12]2=[O:20])[CH2:7][CH2:6]1)[CH3:4]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 15890674178-99-7

Product 1

HCID 12811315HCID 12811315, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2.0 g of 1-[3-hydroxy-3-(3,4-dimethoxyphenyl)-2-propyl]-4-(2-keto-1-benzimidazolinyl)-piperidine and 0.6 g of 4-dimethylaminopyridine in 10 ml of dimethylformamide is stirred at room temperature for 12 hours. Dimethylformamide is distilled away under reduced pressure to obtain a residue. The residue is dissolved in 20 ml of ethyl acetate. To the solution is added 0.6 g of triethylamine. The mixture is washed five times with 20 ml of water and dried. Recrystallization of the crystals from a mixture of dioxane and ether (1:1) yields 1.21 g of 1-[3-hydroxy-3-(3,4-dimethoxyphenyl)-2-propyl]-4-(3-acetyl-2-keto-1-benzimidazolinyl)-piperidine.

Workup

  1. distillationDimethylformamide is distilled away under reduced pressure
  2. customto obtain a residue
  3. washThe mixture is washed five times with 20 ml of water
  4. customdried
  5. customRecrystallization of the crystals
  6. additionfrom a mixture of dioxane and ether (1:1)

Sources & evidence

ORD record
ord-5b1d2c174327470cb94633c0dcd17895
Source dataset
uspto-grants-1984_05
Patent number
US04446141

Reaction notes

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