4-Toluenesulfonyl chloride → HCID 178420354, compound

HRID 1403126Notes

Reaction equation

HRID 1403126 reaction equation
[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([O:15][CH2:16][CH2:17][CH2:18]O)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[NH:44]1[CH2:48][CH2:47][CH2:46][CH2:45]1>O.C(OCC)(=O)C.CN(C)C=O.N1C=CC=CC=1>[CH2:20]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@H:9]1[CH2:10][CH2:11][C@H:12]([O:15][CH2:16][CH2:17][CH2:18][N:44]2[CH2:48][CH2:47][CH2:46][CH2:45]2)[CH2:13][CH2:14]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

9

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 178520891HCID 178520891, compound

Product 1

HCID 178420354HCID 178420354, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 3-{[trans-4-(dibenzylamino)cyclohexyl]oxy}propan-1-ol (110 mg) were added tosyl chloride (60 mg) and pyridine (51 μL) under ice-cooling, followed by stirring at room temperature for 1 hour. To the reaction mixture were added N,N-dimethylformamide (1.1 mL), potassium carbonate (43 mg), and pyrrolidine (26 μL), followed by stirring at room temperature overnight. The reaction mixture were added ethyl acetate and water, and the organic layer was extracted, washed with saturated brine, and then dried over anhydrous magnesium sulfate. Then, the solvent was evaporated under reduced pressure. The residue was purified by amino silica gel column chromatography (hexane:ethyl acetate-90:10-70:30) to obtain trans-N,N-dibenzyl-4-[3-(pyrrolidin-1-yl)propoxy]cyclohexanamine (70 mg).

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature overnight
  3. extractionthe organic layer was extracted
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThen, the solvent was evaporated under reduced pressure
  7. customThe residue was purified by amino silica gel column chromatography (hexane:ethyl acetate-90:10-70:30)

Sources & evidence

ORD record
ord-d1e5ffef29784ffdb164c8f5879b8e12
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

Loading…