Piperidine → 9-(1-Piperidyl)nonanyl isopropyl ether

HRID 2226460Notes

Reaction equation

HRID 2226460 reaction equation
[CH:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]Br)([CH3:3])[CH3:2].[NH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>>[CH:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 8082Piperidine2×HCID 18965285HCID 18965285, compound

Product 1

HCID 152325739-(1-Piperidyl)nonanyl isopropyl etherYield 68.8%

Procedure

Mix 9-bromononanyl isopropyl ether (730 mg, 2.75 mmol) and piperidine (1 mL, 10 mmol) and stir at room temperature overnight. Add additional piperidine (5 mL) and heat at 100° C. for 4 hours. Partition between ethyl ether and 5N sodium hydroxide. Separate the organic phase and extract the aqueous phase with ethyl ether (2×30 mL). Combine the organic phases and dry (MgSO4). Evaporate the solvent in vacuo to yield 510 mg yellow oil. Purify by silica gel chromatography (ethyl acetate followed by 10% MeOH/ethyl acetate) to yield 380 mg (51%) of the title compound as a pale yellow oil.

Workup

  1. temperatureheat at 100° C. for 4 hours
  2. customPartition between ethyl ether and 5N sodium hydroxide
  3. customSeparate the organic phase
  4. extractionextract the aqueous phase with ethyl ether (2×30 mL)
  5. dry with materialCombine the organic phases and dry (MgSO4)
  6. customEvaporate the solvent in vacuo

Sources & evidence

ORD record
ord-d47ee07b20a44f30a0574bae7af1b52a
Source dataset
uspto-grants-1994_09
Patent number
US05348964

Reaction notes

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