Dimethyl Sulfoxide → 1-(2-Phenylethyl)-4-methyl-4-formyl-piperidine

HRID 374465Notes

Reaction equation

HRID 374465 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]1([CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][C:22]([CH3:27])([CH2:25][OH:26])[CH2:21][CH2:20]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)Cl.O>[C:11]1([CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][C:22]([CH3:27])([CH:25]=[O:26])[CH2:21][CH2:20]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 189971411-(2-Phenylethyl)-4-methyl-4-hydroxymethyl-piperidine

Product 1

HCID 189971371-(2-Phenylethyl)-4-methyl-4-formyl-piperidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

A solution of 10 mL of methylene chloride and 0.4 mL (4.4 mmol) of oxalyl chloride was cooled under nitrogen to -60°. A solution of 0.68 mL of dimethylsulfoxide in 2 mL of methylene chloride was added dropwise to the solution. After stirring for 2 minutes 0.95 g (4 mmol) of 1-(2-phenylethyl)-4-methyl-4-hydroxymethyl-piperidine was added in 2-3 mL of methylene chloride. Stirring was continued for an additional 15 minutes. Triethylamine (2.8 mL, 20 mmol) was added to the reaction mixture and stirring was continued for 5 min, then the mixture was allowed to warm to room temperature. Water (20 mL) was added and the aqueous mixture was extracted with methylene chloride. The-organic extracts were washed with brine, dried and evaporated to give 1-(2-phenylethyl)-4-methyl-4-formyl-piperidine as a clear oil in quantitative yield. NMR (CDCl3) δ9.46 (s, 1H); 7.16-7.27 (m, 5H); 2.84-3.00 (br, 1H); 2.75-2.82 (m, 2H); 2.65-2.75 (m, 2H); 2.55-2.63 (m, 2H); 2.27 (t, 2H); 1.98-2.09 (m, 2H); 1.51-1.63 (m, 2H); 1.05 (s, 3H).

Workup

  1. stirringstirring
  2. waitwas continued for 5 min
  3. extractionthe aqueous mixture was extracted with methylene chloride
  4. washThe-organic extracts were washed with brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-66c98e300ce84c89ba793b53e9b82e51
Source dataset
uspto-grants-1996_01
Patent number
US05480892

Reaction notes

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