Methanol → HCID 19029309, compound

HRID 2256304Notes

Reaction equation

HRID 2256304 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:36])[C:9](=O)[CH2:10][CH:11]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=2)[CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16][CH2:15]2)=[CH:4][CH:3]=1.CSC.CO>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:36])[CH2:9][CH2:10][CH:11]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=2)[CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:16][CH2:15]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 19029358HCID 19029358, compound

Product 1

HCID 19029309HCID 19029309, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(4-Chlorophenyl)-beta-(3,4-Dichlorophenyl)-N-methyl-4-(phenylmethyl)-1-piperidinepentanamide (0.38 g) in THF (30 mL) was treated with BH3 :DMS (0.4 mL; 10M) and heated at reflux temperature for 18 hours. The cooled reaction mixture was then treated with MeOH (2.0 mL) and the solvent evaporated under reduced pressure. The residue was dissolved in EtOH (20 mL), treated with potassium carbonate and heated at reflux temperature for 3 hours. The reaction mixture was concentrated under reduced pressure and partitioned between CH2Cl2 (20 mL) and saturated NaHCO3 solution (20 mL). The organic portion was separated and the aqueous rextracted with CH2Cl2 (2×20 mL). The combined organic was dried over MgSO4, filtered and evaporated to give an oil. Silica gel chromatography eluting with 5% MeOH:CH2Cl2 gave the title compound (0.18 g). Mass spectrum (CI): 529.

Workup

  1. temperatureat reflux temperature for 18 hours
  2. customThe cooled reaction mixture
  3. customthe solvent evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in EtOH (20 mL)
  5. additiontreated with potassium carbonate
  6. temperatureheated
  7. temperatureat reflux temperature for 3 hours
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. custompartitioned between CH2Cl2 (20 mL) and saturated NaHCO3 solution (20 mL)
  10. customThe organic portion was separated
  11. dry with materialThe combined organic was dried over MgSO4
  12. filtrationfiltered
  13. customevaporated
  14. customto give an oil
  15. washSilica gel chromatography eluting with 5% MeOH

Sources & evidence

ORD record
ord-8a3f94e1a27c482cb88c27df21796789
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

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