Dimethyl Sulfoxide → 1-(Phenylmethyl)-4-piperidinepropanal

HRID 1386809Notes

Reaction equation

HRID 1386809 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([N:18]1[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][CH2:26][OH:27])[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH2:11]([N:18]1[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][CH:26]=[O:27])[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 11436230HCID 11436230, compound

Product 1

HCID 114589021-(Phenylmethyl)-4-piperidinepropanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of 0.93 mL of oxalyl chloride in 20 mL of CH2Cl2 at −78° C. was added 1.13 mL of DMSO in 0.1 mL of CH2Cl2 dropwise. After stirring 5 min, a solution of 3-(1-benzyl-piperidin)yl)propan-1-ol (form Step C) in 8 mL of CH2Cl2 was added dropwise. After stirring 15 minutes, 0.75 mL of diisopropylethylamine was added. The reaction was warmed to 0° C. and stirred for 20 min. After quenching with H2O, the reaction was diluted with 50 mL of CH2Cl2. The aqueous layer was extracted with 2×50 mL Of CH2Cl2. The combined organic phases were dried over MgSO4 and concentrated to give 612 mg the title compound, which was used for the next step without further purification

Workup

  1. stirringAfter stirring 15 minutes
  2. stirringstirred for 20 min
  3. customAfter quenching with H2O
  4. additionthe reaction was diluted with 50 mL of CH2Cl2
  5. extractionThe aqueous layer was extracted with 2×50 mL Of CH2Cl2
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-257b0e5cde3a4d818aee17d296e00f87
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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