4-Iodobenzoyl chloride → (4-Dimethylamino-piperidin-1-yl)-(4-iodo-phenyl)-methanone

HRID 529768Notes

Reaction equation

HRID 529768 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH3:11][N:12]([CH3:19])[CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>[CH3:11][N:12]([CH3:19])[CH:13]1[CH2:18][CH2:17][N:16]([C:6]([C:5]2[CH:9]=[CH:10][C:2]([I:1])=[CH:3][CH:4]=2)=[O:7])[CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 743734-Iodobenzoyl chlorideHCID 417391N,N-Dimethylpiperidin-4-amine

Product 1

HCID 60763941(4-Dimethylamino-piperidin-1-yl)-(4-iodo-phenyl)-methanoneYield 98%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

A solution of 4-iodo-benzoyl chloride (4.72 g, 17.71 mmol) in DCM (70 mL) at 0° C. was treated with dimethyl-piperidin-4-yl-amine (2.27 g, 17.71 mmol). The resultant suspension was warmed to room temperature and stirred for 2.5 hours. The reaction mixture was diluted with 1M aqueous Na2CO3 solution and the phases separated. The aqueous phase was extracted twice with DCM and the combined organic phase was dried (Na2SO4) and evaporated to afford (4-dimethylamino-piperidin-1-yl)-(4-iodo-phenyl)-methanone as a white solid (6.2 g, 98%). LCMS (Method 3) [M+H]+=359.2, RT=1.82 min.

Workup

  1. customthe phases separated
  2. extractionThe aqueous phase was extracted twice with DCM
  3. dry with materialthe combined organic phase was dried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-84f75af1e6c94959a334d320bd58640e
Source dataset
uspto-grants-2016_05
Patent number
US09346815B2

Reaction notes

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