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Dimethyl Sulfoxide → HCID 19898851, compound

HRID 1196518
Notes
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Reaction equation

HRID 1196518 reaction equation
CS(C)=O.C(Cl)(=O)C([Cl:8])=O.Cl.[Cl:12][C:13]1[CH:14]=[C:15]([CH2:20][C:21]([N:23]2[CH2:28][CH2:27][CH2:26][C@@H:25]([OH:29])[C@@H:24]2[CH2:30][N:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)=[O:22])[CH:16]=[CH:17][C:18]=1[Cl:19].C(N(CC)CC)C>ClCCl.O>[ClH:8].[Cl:12][C:13]1[CH:14]=[C:15]([CH2:20][C:21]([N:23]2[CH2:28][CH2:27][CH2:26][C:25](=[O:29])[CH:24]2[CH2:30][N:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)=[O:22])[CH:16]=[CH:17][C:18]=1[Cl:19]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 67916857trans-1-[(3,4-Dichlorophenyl)acetyl]-2-(1-pyrrolidinylmethyl)-3-piperidinol hydrochloride

Product 1

HCID 19898851HCID 19898851, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
20 °C

Procedure

Dimethylsulphoxide (0.925 g) in dry dichloromethane (3 ml) was added dropwise to a stirred solution of oxalyl chloride (0.753 g) in dichloromethane (12 ml) at -60° under nitrogen, so as to maintain the internal temperature below -50°. The reaction mixture was stirred for 3 min before adding a solution of the product of Example 4 (2.0 g) in dichloromethane (5 ml) over 5 min. Stirring was continued for 15 min at -60° and triethylamine (2.72 g) was added with stirring. The reaction mixture was allowed to warm to 20° C., water (30 ml) was added, the layers were separated and the aqueous layer was further extracted with dichloromethane (30 ml). The combined organic extracts were dried and concentrated in vacuo to give a solid which was triturated under dry diethyl ether to give the free base of the title compound as an amorphous solid (1.54 g), m.p. 74°-76°. A portion (100 mg) of the free base was dissolved in a minimum amount of diethyl ether/ethyl acetate and treated with ethereal hydrogen chloride to precipitate the title compound as an amorphous solid (85 mg) m.p. 145°-147° (decomp.)

Workup

  1. temperatureso as to maintain the internal temperature below -50°
  2. stirringStirring
  3. waitwas continued for 15 min at -60°
  4. stirringwith stirring
  5. customthe layers were separated
  6. extractionthe aqueous layer was further extracted with dichloromethane (30 ml)
  7. customThe combined organic extracts were dried
  8. concentrationconcentrated in vacuo
  9. customto give a solid which
  10. customwas triturated under dry diethyl ether

Sources & evidence

ORD record
ord-c4b336cc683e4a94879655599c046290
Source dataset
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05114945

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes