Piperidine → HCID 18472223, compound

HRID 1387857Notes

Reaction equation

HRID 1387857 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[S:17][CH2:16][CH2:15][C:14]([C:18]([NH:20][C:21]4[CH:26]=[CH:25][C:24](O)=[CH:23][C:22]=4C)=[O:19])=[CH:13][C:12]=3[CH:29]=2)=[CH:4][CH:3]=1.CN([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=1)C.[CH3:39]S(Cl)(=O)=O.N1CCCCC1>O1CCCC1.C(N(CC)CC)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[S:17][CH2:16][CH2:15][C:14]([C:18]([NH:20][C:21]4[CH:22]=[CH:23][C:24]([CH2:39][N:34]5[CH2:35][CH2:36][CH2:37][CH2:38][CH2:33]5)=[CH:25][CH:26]=4)=[O:19])=[CH:13][C:12]=3[CH:29]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chlorideHCID 69354060HCID 69354060, compound

Product 1

HCID 18472223HCID 18472223, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 7-(4-methylphenyl)-N-(4-hydroxy-methylphenyl)-2,3-dihydro-1-benzothiepine-4-carboxamide (0.2 g), triethylamine (0.21 ml) and dimethylaminopyridine (catalytic amount) in tetrahydrofuran (10 ml) was dropwise added methane-sulfonylchloride (0.06 ml) under ice-cooling, and the mixture was stirred for 10 minutes. To the mixture was added piperidine (0.15 ml), and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated, and to the residue was added water. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column (methanol/triethylamine/ethyl acetate) to give crude crystals, which were recrystallized from ethyl acetate-hexane to give 7-(4-methylphenyl)-N-(4-piperidinomethylphenyl)-2,3-dihydro-1-benzothiepine-4-carboxamide (Compound 93) (0.19 g) as colorless crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. customThe solvent was evaporated
  4. additionto the residue was added water
  5. extractionThe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated sodium chloride solution
  7. dry with materialdried with anhydrous magnesium sulfate
  8. customUnder reduced pressure, the solvent was evaporated
  9. customthe residue was purified with silica gel column (methanol/triethylamine/ethyl acetate)
  10. customto give crude crystals, which
  11. customwere recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-406f3432c1dc4414ac1bf32aa34aa545
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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