Potassium Iodide → 3-(3-(4-benzylpiperidin-1-yl)propyl)-6,7,8,9-tetrahydro-5H-1,2,4-triazolo[4,3-a]azepine

HRID 635272Notes

Reaction equation

HRID 635272 reaction equation
CS(Cl)(=O)=O.O[CH2:7][CH2:8][CH2:9][C:10]1[N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:13]2=[N:12][N:11]=1.[CH2:20]([CH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O.O.C(N(CC)CC)C>[CH2:20]([CH:27]1[CH2:32][CH2:31][N:30]([CH2:7][CH2:8][CH2:9][C:10]2[N:14]3[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:13]3=[N:12][N:11]=2)[CH2:29][CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

9

Reactant 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 317384-BenzylpiperidineHCID 246884223-(3-hydroxypropyl)-6,7,8,9-tetrahydro-5H-1,2,4-triazolo[4,3-a]azepine

Product 1

HCID 155211573-(3-(4-benzylpiperidin-1-yl)propyl)-6,7,8,9-tetrahydro-5H-1,2,4-triazolo[4,3-a]azepine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Triethylamine (1.4 ml) and methanesulfonyl chloride (0.62 ml) were added to a solution of 3-(3-hydroxypropyl)-6,7,8,9-tetrahydro-5H-1,2,4-triazolo[4,3-a]azepine (0.98 g) obtained in the same manner as in Example 4 in dimethylformamide (20 ml) with stirring. Then, 4-benzylpiperidine (0.88 g), potassium carbonate (1.38 g) and potassium iodide (0.83 g) were added and the mixture was stirred for 4 hours at 60° C. After the completion of the reaction, the reaction mixture was poured into water, extracted with ethyl acetate, washed with water, and dried over magnesium sulfate. The solution was concentrated under reduced pressure to give 3-(3-(4-benzylpiperidin-1-yl)propyl)-6,7,8,9-tetrahydro-5H-1,2,4-triazolo[4,3-a]azepine.

Workup

  1. stirringthe mixture was stirred for 4 hours at 60° C
  2. customAfter the completion of the reaction
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bf5ce4330df84541bd33667931603c63
Source dataset
uspto-grants-2001_02
Patent number
US06187774B1

Reaction notes

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