Thionyl Chloride → 5-(4-Ethylphenyl)-1-(morpholin-4-ylcarbonyl)piperidine-3-carbonyl chloride

HRID 1642855Notes

Reaction equation

HRID 1642855 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][N:13]([C:15]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[O:16])[CH2:12][CH:11]([C:23]([OH:25])=O)[CH2:10]2)=[CH:5][CH:4]=1)[CH3:2].S(Cl)([Cl:28])=O>ClCCl>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][N:13]([C:15]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[O:16])[CH2:12][CH:11]([C:23]([Cl:28])=[O:25])[CH2:10]2)=[CH:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 580022255-(4-Ethylphenyl)-1-(morpholin-4-ylcarbonyl)piperidine-3-carboxylic acid

Product 1

HCID 580024315-(4-Ethylphenyl)-1-(morpholin-4-ylcarbonyl)piperidine-3-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

150 mg (0.43 mmol) of the compound from Example 38A were initially charged in 3 ml of dichloromethane, and 63 μl (103 mg, 0.87 mmol) of thionyl chloride were added. The reaction mixture was stirred under RF for 2 h, concentrated under reduced pressure, and then three times toluene was added and the mixture was in each case concentrated again under reduced pressure.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionthree times toluene was added
  3. concentrationconcentrated again under reduced pressure

Sources & evidence

ORD record
ord-e866da0dd2824ddc918a96de6546f743
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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