Acetyl chloride → 1-Acetyl-4-[[[4-(2-butynyloxy)phenyl]sulfonyl]methyl]-4-piperidinecarboxylic Acid, Ethyl Ester

HRID 278337Notes

Reaction equation

HRID 278337 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]#[C:25][CH3:26])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].C(N(CC)CC)C.[C:34](Cl)(=[O:36])[CH3:35]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:34]([N:9]1[CH2:8][CH2:7][C:6]([CH2:12][S:13]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]#[C:25][CH3:26])=[CH:20][CH:21]=2)(=[O:15])=[O:14])([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:11][CH2:10]1)(=[O:36])[CH3:35]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 22626999HCID 22626999, compound

Product 1

HCID 865854121-Acetyl-4-[[[4-(2-butynyloxy)phenyl]sulfonyl]methyl]-4-piperidinecarboxylic Acid, Ethyl EsterYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-[[[4-(2-Butynyloxy)phenyl]sulfonyl]methyl]-4-piperidinecarboxylic acid ethyl ester (0.24 g, 0.576 mmol), triethylamine (0.32 ml) and catalytic amount of 4-Dimethylaminopyridine in 6.0 mL of CH2Cl2 was added a solution of acetyl chloride (0.068 ml, 0.864 mmol) in 1.0 mL of CH2Cl2. The reaction stirred at room temperature for 4 h and washed with H2O, brine, dried over MgSO4, filtered through a pad of silica gel and concentrated to provide 0.242 g (100%) of the desired product as a colorless gum. Electrospray Mass Spec: 422.2 (M+H)+

Workup

  1. washwashed with H2O, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered through a pad of silica gel
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ccfaafd3455a41bd8da1c455df8620cc
Source dataset
uspto-grants-2002_03
Patent number
US06358980B1

Reaction notes

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