Hydrochloric Acid → HCID 131721528, compound

HRID 613245Notes

Reaction equation

HRID 613245 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:29]=[CH:28][C:7]([C:8]([NH:10][C@H:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][C@H:12]2[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)=O)=[CH:6][CH:5]=1.[ClH:31]>C(#N)C.O=P(Cl)(Cl)Cl>[ClH:31].[CH3:25][O:24][C:21]1[C:20]([O:26][CH3:27])=[CH:19][C:18]2[C@H:12]3[C@H:11]([CH2:16][CH2:15][N:14]([CH3:17])[CH2:13]3)[N:10]=[C:8]([C:7]3[CH:28]=[CH:29][C:4]([C:3]([O:2][CH3:1])=[O:30])=[CH:5][CH:6]=3)[C:23]=2[CH:22]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131721530HCID 131721530, compound

Product 1

HCID 131721528HCID 131721528, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 24813Phosphorus oxychlorideSolvent

Procedure

2.31 g of (-)-cis-terephthalic acid N-[3-(3,4-dimethoxyphenyl)-1-methylpiperidin-4-yl]amide mono-methyl ester are heated to boiling under reflux for 4 h in 25 ml of acetonitrile and 3 ml of phosphorus oxytrichloride. After distilling off the excess phosphorus oxytrichloride, the residue is partitioned between dichloromethane and saturated sodium hydrogencarbonate solution. The organic phase is washed with water, dried over sodium sulfate and concentrated. The solid residue is purified by silica gel chromatography, the main product fraction is separated and this is concentrated. The solid residue is dissolved in a little methanol, and the solution is treated with one equivalent of aqueous HCl and concentrated. The solid residue is recrystallized in methanol/diethyl ether. 1.76 g (70% of theory) of the title compound are obtained as a 1.25-hydrochloride 0.5-hydrate having the m.p. 188-192° C. (unsharp, slow deliquescence).

Workup

  1. distillationAfter distilling off the excess phosphorus oxytrichloride
  2. customthe residue is partitioned between dichloromethane and saturated sodium hydrogencarbonate solution
  3. washThe organic phase is washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe solid residue is purified by silica gel chromatography
  7. customthe main product fraction is separated
  8. concentrationthis is concentrated
  9. dissolutionThe solid residue is dissolved in a little methanol
  10. concentrationconcentrated
  11. customThe solid residue is recrystallized in methanol/diethyl ether

Sources & evidence

ORD record
ord-e5e993b51ec845c4969529a08041ad25
Source dataset
uspto-grants-1999_12
Patent number
US06008215

Reaction notes

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