Acetyl chloride → HCID 69309773, compound

HRID 269980Notes

Reaction equation

HRID 269980 reaction equation
[O:1]1[CH2:6][CH2:5]OCC1.Cl.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=2[I:28])[CH2:17][CH2:16]1)=O)(C)(C)C.C(N(CC)CC)C.C(Cl)(=O)C>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOCC>[Cl:27][C:25]1[CH:24]=[CH:23][C:22]([I:28])=[C:21]([CH:18]2[CH2:19][CH2:20][N:15]([C:6](=[O:1])[CH3:5])[CH2:16][CH2:17]2)[CH:26]=1

Participants

8

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 204431481,4-Dioxane hydrochlorideHCID 69310813HCID 69310813, compound

Product 1

HCID 69309773HCID 69309773, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Add a 4N HCl dioxane solution (604 μL, 2.42 mmol) to a solution of 4-(5-chloro -2-iodo-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (prepared according to preparation 70, 170 mg, 0.40 mmol) in CH2Cl2 (6 mL) at room temperature under argon, and stir the mixture overnight. Add triethylamine (450 μL, 3.20 mmol), DMAP (catalytic amount) and acetyl chloride (56 μL, 0.80 mmol), and stir the mixture overnight. Quench the reaction by addition of Et2O, wash with 1N NaOH and water, dry over MgSO4 and concentrate to afford 1-[4-(5-chloro-2-iodo-phenyl)-piperidin-1-yl]-ethanone. Purify the crude product by flash chromatography on silica gel, eluent hexane/EtOAc 3:2 (65% yield). Follow a procedure similar to preparation 49 substituting 1-[4-(5-chloro-2-iodo-phenyl)-piperidin-1-yl]-ethanone for 1-(5-chloro-2-iodo-phenyl)-pyrrolidine to obtain the title compound.

Workup

  1. customQuench
  2. customthe reaction
  3. washwash with 1N NaOH and water
  4. dry with materialdry over MgSO4
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-382c9865a2394b8fbbd49ecd46a3e1eb
Source dataset
uspto-grants-2008_11
Patent number
US07449477B2

Reaction notes

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