Potassium Carbonate → HCID 15895341, compound

HRID 1955178Notes

Reaction equation

HRID 1955178 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:12]1([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CCO>[O:1]([CH2:8][CH2:9][CH2:10][N:21]1[CH2:22][CH2:23][CH:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:19][CH2:20]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68522Benzene, (3-bromopropoxy)-HCID 698734-Phenylpiperidine

Product 1

HCID 15895341HCID 15895341, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-phenoxypropyl bromide (224 mg, 1.04 mmol), 4-phenylpiperidine (140 mg, 0.870 mmol) and K2CO3 (264 mg, 1.91 mmol) in 15 mL of EtOH was refluxed under N2 for 12 hr. The inorganic salt was removed through a short column of silica gel and washed with EtOAc (3×15 mL). The filtrate was evaporated in vacuo to give a residue, which was purified by flash chromatography giving the title as a pale yellow oil (165 mg, 64%): 1H NMR (CDCl3) 1.90 (m, 4 H), 2.10 (m, 4 H), 2.55 (m, 1H), 2.70 (bs, 2 H), 3.20 (bs, 2 H), 4.05 (m, 2 H), 6.92 (m, 4 H), 7.29 (m, 6 H).

Workup

  1. temperaturewas refluxed under N2 for 12 hr
  2. customThe inorganic salt was removed through a short column of silica gel
  3. washwashed with EtOAc (3×15 mL)
  4. customThe filtrate was evaporated in vacuo
  5. customto give a residue, which
  6. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-827851f20ac742cbb35e8ad1319c2d1f
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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