Dimethyl Sulfoxide → HCID 11780885, compound

HRID 1199354Notes

Reaction equation

HRID 1199354 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][C@H:12]1[C@H:17]([C:18]2[C:23]([O:24][CH3:25])=[CH:22][C:21]([O:26][CH3:27])=[CH:20][C:19]=2[O:28][CH3:29])[CH2:16][CH2:15][N:14]([CH3:30])[CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.O.C(N(CC)CC)C>[CH3:30][N:14]1[CH2:15][CH2:16][CH:17]([C:18]2[C:23]([O:24][CH3:25])=[CH:22][C:21]([O:26][CH3:27])=[CH:20][C:19]=2[O:28][CH3:29])[C:12](=[O:11])[CH2:13]1

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10340Sodium CarbonateHCID 65578Oxalyl chlorideHCID 68880556HCID 68880556, compound

Product 1

HCID 11780885HCID 11780885, compoundYield 76.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
-30 °C

Procedure

Dimethyl sulfoxide (35 ml) is added dropwise under nitrogen to a solution, cooled to -60° C., of oxalyl chloride (20 ml) in dry methylene chloride (500 ml), and the mixture is stirred for 5-10 minutes. A solution of (±)-trans-3-hydroxy-4-(2,4,6-trimethoxyphenyl)-1-methylpiperidine (62 g) in methylene chloride (300 ml) is then added, while the temperature of the reaction mixture is held at -60° C. After the addition, the mixture is stirred for 15 minutes and triethylamine (155 ml) is added. The reaction mixture is then allowed to warm to a temperature of -30° C., diluted with water and rendered alkaline with sodium carbonate. The organic layer is separated off and the aqueous layer is extracted with ethyl acetate. The organic layers are combined, washed with brine, dried over anhydrous Na2SO4 and concentrated to give a solid residue which, on crystallization from isopropanol, gives the desired product (47 g) of melting point 110°-112° C.

Workup

  1. customis held at -60° C
  2. additionAfter the addition
  3. stirringthe mixture is stirred for 15 minutes
  4. customThe organic layer is separated off
  5. extractionthe aqueous layer is extracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. customto give a solid residue which
  10. customon crystallization from isopropanol

Sources & evidence

ORD record
ord-a3302428993942ed846b47a39a5c4df0
Source dataset
uspto-grants-1990_02
Patent number
US04900727

Reaction notes

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