p-Fluorophenyl 4-piperidyl ketone hydrochloride → HCID 178453902, compound

HRID 420762Notes

Reaction equation

HRID 420762 reaction equation
Cl.[F:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.[C:17]([O:21][C:22](=[O:33])[NH:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([CH2:30][CH:31]=O)[CH2:26][CH2:25]1)([CH3:20])([CH3:19])[CH3:18].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:17]([O:21][C:22](=[O:33])[NH:23][C@H:24]1[CH2:25][CH2:26][C@H:27]([CH2:30][CH2:31][N:12]2[CH2:13][CH2:14][CH:9]([C:7](=[O:8])[C:6]3[CH:5]=[CH:4][C:3]([F:2])=[CH:16][CH:15]=3)[CH2:10][CH2:11]2)[CH2:28][CH2:29]1)([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 178453924HCID 178453924, compound

Product 1

HCID 178453902HCID 178453902, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(4-fluorobenzoyl)piperidine hydrochloride (0.850 g, 3.4 mmol), trans-[4-(2-Oxo-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester (0.926 g, 4 mmol), in dichloromethane (10 mL) was stirred for 2 hours at room temperature and sodium triacetoxyborohydride (1.33 g, 6 mmol) was added and the resulting solution was stirred for 12 hours until the TLC indicated completion of the reaction. The mixture was filtrated and concentrated to dryness and purified with column chromatography on silica gel using CH2Cl2—CH2Cl2/MeOH (1-9:1). The product fractions were concentrated to give 1.4 g (3.25 mmol, 93.2% yield) of a light yellow solid. MS (m/e): 433.4 (M+H+).

Workup

  1. customcompletion of the reaction
  2. filtrationThe mixture was filtrated
  3. concentrationconcentrated to dryness
  4. custompurified with column chromatography on silica gel
  5. concentrationThe product fractions were concentrated

Sources & evidence

ORD record
ord-b53cef4b3c12404ba0bfe816a1c769d5
Source dataset
uspto-grants-2012_01
Patent number
US08097637B2

Reaction notes

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