Hydrochloric Acid → HCID 86660738, compound

HRID 1048529Notes

Reaction equation

HRID 1048529 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[NH:12][C:11](=[O:21])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Cl.C1(C)C=CC=CC=1.C([O:32]CC)C>>[Cl-:1].[C:11]([CH2:10][CH2:9][C@H:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[C@@H:13]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[NH3+:12])([OH:21])=[O:32]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 3283Diethyl EtherHCID 58573791(5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)piperidin-2-one

Product 1

HCID 86660738HCID 86660738, compound

Procedure

A suspension of (5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)piperidin-2-one (Example 1, Step E, 29 g, 91 mmol) in 5 M hydrochloric acid (91 mL, 453 mmol) was brought to reflux. After 2 h, TLC indicated complete consumption of starting material to the ring opened product (elution with 75% ethyl acetate in hexanes; Rf starting material=0.5, Rf product=0.0). The reaction contents were co-distilled with toluene (4×100 mL) then brought to dryness. Solids were suspended in diethyl ether (100 mL), filtered, and washed with ether (100 mL). The white crystalline solid was brought to dryness under high vacuum to provide the title compound.

Workup

  1. temperatureto reflux
  2. customconsumption of starting material to the ring
  3. washproduct (elution with 75% ethyl acetate in hexanes; Rf starting material=0.5, Rf product=0.0)
  4. customThe reaction contents
  5. filtrationfiltered
  6. washwashed with ether (100 mL)

Sources & evidence

ORD record
ord-25cfcc553b494282b9cd09ce988c13ff
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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