Piperidine → HCID 18965299, compound

HRID 2226473Notes

Reaction equation

HRID 2226473 reaction equation
[CH2:1]([S:8]([CH2:11][CH2:12]Cl)(=[O:10])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>>[CH2:1]([S:8]([CH2:11][CH2:12][N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)(=[O:10])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

3

Reactant 2

HCID 8082Piperidine2×HCID 12518282HCID 12518282, compound

Product 1

HCID 18965299HCID 18965299, compound

Conditions

Temperature
60 °C

Procedure

Mix 2-chloroethyl heptyl sulfone (1.1 g, 5 mmol) and piperidine (10 mL). Stir at 60° C. overnight. Add addition piperidine (5 mL) and stir at 60° C. overnight. Cool to room temperature, partition between 5N sodium hydroxide and ethyl ether. Separate the organic phase and extract the aqueous phase with ethyl ether (2×25 mL). Combine the organic phases, dry (MgSO4) and evaporate in vacuo to yield 1.2 g orange oil which crystallizes. Purify by silica gel chromatography (ethyl acetate) to yield 930 mg. Purify again by silica gel chromatography (hexane, then 10% ethyl acetate/hexane, then 50% ethyl acetate/hexane) to yield 360 mg of the title compound as a yellow oil.

Workup

  1. additionAdd
  2. stirringstir at 60° C. overnight
  3. temperatureCool to room temperature
  4. custompartition between 5N sodium hydroxide and ethyl ether
  5. customSeparate the organic phase
  6. extractionextract the aqueous phase with ethyl ether (2×25 mL)
  7. dry with materialCombine the organic phases, dry (MgSO4)
  8. customevaporate in vacuo

Sources & evidence

ORD record
ord-12f1c175fcb544e19b75f47966ab2c05
Source dataset
uspto-grants-1994_09
Patent number
US05348964

Reaction notes

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