Potassium Carbonate → 4-Benzhydryl-1-(3-hydroxypropyl)piperidine

HRID 366420Notes

Reaction equation

HRID 366420 reaction equation
[CH:1]([CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].C(N(C(C)C)CC)(C)C.Br[CH2:36][CH2:37][CH2:38][OH:39]>C(O)CCC>[CH:1]([CH:14]1[CH2:19][CH2:18][N:17]([CH2:36][CH2:37][CH2:38][OH:39])[CH2:16][CH2:15]1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 81531DiisopropylethylamineHCID 882784-Benzhydrylpiperidine

Product 1

HCID 117712884-Benzhydryl-1-(3-hydroxypropyl)piperidine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

4-Benzhydrylpiperidine (10 mmol, 2.87 g) is slurried in n-butanol (30 mL), and K2CO3 (s) (2.76 g, 10 mmol) or diisopropylethylamine (20 mmol, 2.5 g) and 3-bromopropanol (10 mmol, 1.39 g) are added to the slurry. The stirred mixture is refluxed for about 7 hours under N2 (g), filtered, and concentrated in vacuo. The residue is dissolved in hot CHCl3, filtered and concentrated in vacuo to yield crude product as an oil (3.0-3.1 g) which is used without further purification.

Workup

  1. temperatureThe stirred mixture is refluxed for about 7 hours under N2 (g)
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue is dissolved in hot CHCl3
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6341d46852a047ecbe4c9f4005807857
Source dataset
uspto-grants-2000_10
Patent number
US06130217

Reaction notes

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