4-(4-Fluorobenzoyl)piperidine → HCID 178523664, compound

HRID 1961625Notes

Reaction equation

HRID 1961625 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.O=[CH:17][CH2:18][C@H:19]1[CH2:24][CH2:23][C@H:22]([NH:25][C:26]([C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:31]=[CH:30][CH:29]=2)=[O:27])[CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:17][CH2:18][C@H:19]3[CH2:24][CH2:23][C@H:22]([NH:25][C:26]([C:28]4[C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[N:31]=[CH:30][CH:29]=4)=[O:27])[CH2:21][CH2:20]3)[CH2:10][CH2:9]2)=[O:7])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 27244404-(4-Fluorobenzoyl)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 178520748HCID 178520748, compound

Product 1

HCID 178523664HCID 178523664, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(4-fluorobenzoyl)piperidine (trifluoro-acetic acid salt) (0.020 g, 0.062 mmol) was solved in 1,2-dichloromethane (0.300 mL) and Quinoline-4-carboxylic acid trans-[4-(2-oxo-ethyl)-cyclohexyl]-amide (0.020 g, 0.067 mmol) was added. Methanol (0.200 mL) was added to the mixture and it was stirred overnight. Sodium triacetoxyborohydride (0.024, 0.11 mmol) was added to the clear solution that was stirred 10 hours at room temperature. The mixture was concentrated to dryness and the residue was taken up on methanol and purified with preparative HPLC on reversed phase eluting with acetonitrile/water. The combined producted fractions were evaporated under reduced pressure to yield 0.03 g of a white solid (0.06 mmol, 99%). MS (m/e): 488.3 (M+H+)

Workup

  1. stirringwas stirred 10 hours at room temperature
  2. concentrationThe mixture was concentrated to dryness
  3. custompurified with preparative HPLC on reversed phase
  4. washeluting with acetonitrile/water
  5. customwere evaporated under reduced pressure

Sources & evidence

ORD record
ord-d3c5d954372f4222869b2a2f9948f126
Source dataset
uspto-grants-2013_04
Patent number
US08415350B2

Reaction notes

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