1,2-Dichloroethane → (4-Bromo-phenyl)-(3-phenyl-piperidin-1-yl)-methanone

HRID 737097Notes

Reaction equation

HRID 737097 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.Cl.[C:12]1([CH:18]2[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:20]2[CH2:21][CH2:22][CH2:23][CH:18]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:19]2)=[O:8])=[CH:9][CH:10]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 114644-Bromobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 173900083-Phenylpiperidine hydrochloride

Product 1

HCID 57849622(4-Bromo-phenyl)-(3-phenyl-piperidin-1-yl)-methanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The above compound could be made in the following manner, analogous to Example 60. 1 eq. of p-Bromobenzoic acid could be combined with 1 eq. 3-Phenylpiperidine HCl, 1.1 equivalents EDC, 1.1 equivalents HOBt and 2.2 equivalents Hunig's Base in DMF (concentration of 1 mL of DMF/mmol acid) would be stirred at room temperature overnight. The solution would then be diluted with water and extracted with ethyl acetate. The organic layers would then be combined and washed with water, aqueous saturated sodium bicarbonate solution, 1N HCl and brine. The organic layers would be dried with sodium sulfate, filtered and concentrated. Purification would be done with flash chromatography to afford product.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water, aqueous saturated sodium bicarbonate solution, 1N HCl and brine
  3. dry with materialThe organic layers would be dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification
  7. customto afford product

Sources & evidence

ORD record
ord-efadde4b28694462be1d6f775c35101b
Source dataset
uspto-grants-2009_09
Patent number
US07595397B2

Reaction notes

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