4-Benzhydryloxypiperidine → HCID 178470490, compound

HRID 2202602Notes

Reaction equation

HRID 2202602 reaction equation
[CH:1]([O:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:21]([C:23]1[C:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N:25][NH:26][CH:27]=1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH:1]([O:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:23]2[C:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N:25][NH:26][CH:27]=2)[CH2:17][CH2:16]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 30175844-BenzhydryloxypiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 178470492HCID 178470492, compound

Product 1

HCID 178470490HCID 178470490, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Benzhydryloxypiperidine (1.0 g, 3.7 mmol) synthesized in Production Example 1, ethyl 4-formylpyrazole-3-carboxylate (630 mg, 3.7 mmol), and dichloromethane (30 mL) were fed to the system, and the atmosphere of the system was replaced with argon gas, and the system was cooled by ice. At 0° C., sodium triacetoxyborohydride (1.2 g, 5.6 mmol) was added thereto, and the mixture was heated to a room temperature. After the disappearance of the raw material was confirmed by TLC, the reaction mixture was quenched with a saturated sodium hydrogen carbonate solution. The reaction mixture was separated into a water layer and an organic layer, and the water layer was extracted with dichloromethane again. The extract was combined to the organic layer. The combined organic layer was dried over sodium sulfate, and the solvent was distilled off. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the title compound (1.3 g, 83%).

Workup

  1. temperaturethe system was cooled by ice
  2. customthe reaction mixture was quenched with a saturated sodium hydrogen carbonate solution
  3. customThe reaction mixture was separated into a water layer
  4. extractionan organic layer, and the water layer was extracted with dichloromethane again
  5. dry with materialThe combined organic layer was dried over sodium sulfate
  6. distillationthe solvent was distilled off
  7. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-f2a341e46de442e5a476274a794210ad
Source dataset
uspto-grants-2016_06
Patent number
US09365553B2

Reaction notes

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