Hydrochloric Acid → HCID 58137244, compound

HRID 1424572Notes

Reaction equation

HRID 1424572 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][CH2:12][C:11]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:15]([OH:17])=O)[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[Al+3].[Cl-].[Cl-].[Cl-].Cl>C(Cl)Cl>[C:1]([N:9]1[CH2:14][CH2:13][CH2:12][C:11]2([CH2:18][C:19]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:15]2=[O:17])[CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 58137328HCID 58137328, compound

Product 1

HCID 58137244HCID 58137244, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A mixture of 1-benzoyl-3-benzyl-piperidine-3-carboxylic acid (6.71 g, 20.7 mmol) and thionyl chloride (2.70 g, 22.77 mmol) in dry CH2Cl2 (25 mL) was heated to reflux for 30 min. The resulting solution was concentrated in vacuum to give alight brown oil. A solution of this oil in dry CH2Cl2 (25 mL) was added dropwise to a mixture of AlCl3 (3.59 g, 26.91 mmol) in CH2Cl2 (10 mL) at 0° C. The mixture was stirred for 15 min at 0° C. and then heated to reflux for 45 min. The mixture was cooled and poured onto crushed ice and 12 N aq HCl. The organic layer was separated, washed with 3 N aq HCl, saturated Na2CO3, water and brine. Finally the organic layer was concentrated to give a residue, which was purified by silica gel column chromatography (petroleum/ethyl acetate 5:1 to 1:1) to afford 1′-benzoylspiro[indene-2,3′-piperidin]-1(3H)-one (3.24 g, 51%). 1H NMR (CD3OD, 400 MHz): δ=1.61 (m, 4H), 2.68 (m, 2H), 3.46 (m, 4H), 7.34 (m, 8H), 7.64 (m, 2H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 30 min
  3. concentrationThe resulting solution was concentrated in vacuum
  4. customto give alight brown oil
  5. temperatureheated
  6. temperatureto reflux for 45 min
  7. temperatureThe mixture was cooled
  8. additionpoured
  9. customThe organic layer was separated
  10. washwashed with 3 N aq HCl, saturated Na2CO3, water and brine
  11. concentrationFinally the organic layer was concentrated
  12. customto give a residue, which
  13. customwas purified by silica gel column chromatography (petroleum/ethyl acetate 5:1 to 1:1)

Sources & evidence

ORD record
ord-f455ab7ff0504a9d8c0e749b01156f66
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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