HCID 70022381, compound → HCID 131723210, compound

HRID 1934342Notes

Reaction equation

HRID 1934342 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C@H:12]2[C@@H:17]([NH:18][C:19](=O)[C:20]3[CH:25]=[CH:24][C:23]([NH:26][S:27]([C:30]4[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=4)(=[O:29])=[O:28])=[CH:22][CH:21]=3)[CH2:16][CH2:15][N:14]([CH3:38])[CH2:13]2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2]>P(Cl)(Cl)(Cl)=O.C(#N)C>[CH2:1]([O:3][C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]2[C:19]([C:20]3[CH:25]=[CH:24][C:23]([NH:26][S:27]([C:30]4[CH:31]=[CH:32][C:33]([CH3:36])=[CH:34][CH:35]=4)(=[O:28])=[O:29])=[CH:22][CH:21]=3)=[N:18][C@@H:17]3[C@H:12]([C:6]=2[CH:5]=1)[CH2:13][N:14]([CH3:38])[CH2:15][CH2:16]3)[CH3:2]

Participants

4

Reactant 1

HCID 70022381HCID 70022381, compound

Product 1

HCID 131723210HCID 131723210, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 24813Phosphorus oxychlorideSolvent2×

Procedure

2.52 g (−)-cis-3-(3-Ethoxy-4-methoxyphenyl)-1-methyl-4-[4-(p-toluenesulfonamido)-benzamido]-piperidine are heated to boiling under reflux for 5 h in 4.3 ml phosphorus oxychloride and 60 ml of acetonitrile. After destilling off the excess acetonitrile and phosphorus oxychloride, the residue is partitioned between dichloromethane and saturated sodium hydrogencarbonate solution. The organic phase is washed with water, dried over sodium sulfate and concentrated. After evaporation of the dichloromethane, the residue is purified over silica gel by chromatography. The main product fraction is separated and concentrated. The title compound is obtained after recrystallisation in ethyl acetate/diethyl ether (1:10) as faint yellow fine crystalls. M.p. 207-219° C. (unsharp, destruction and red colouring).

Workup

  1. customthe residue is partitioned between dichloromethane and saturated sodium hydrogencarbonate solution
  2. washThe organic phase is washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customAfter evaporation of the dichloromethane
  6. customthe residue is purified over silica gel by chromatography
  7. customThe main product fraction is separated
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e0eee0e2bb6b4e278d009ed2c5f46abc
Source dataset
uspto-grants-2002_05
Patent number
US06384047B1

Reaction notes

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