Piperidine → HCID 18965251, compound

HRID 2226464Notes

Reaction equation

HRID 2226464 reaction equation
[CH2:1]([S:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]Cl)=[O:7])[CH2:2][CH:3]([CH3:5])[CH3:4].[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>>[CH2:1]([S:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:7])[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

3

Reactant 2

HCID 8082PiperidineHCID 18965288HCID 18965288, compound

Product 1

HCID 18965251HCID 18965251, compound

Procedure

Heat 5-chloropentyl isopentyl sulfoxide (760 mg, 3.38 mmoL) and piperidine (2 mL) at 125° C. for 1 hour. 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 and dry (MgSO4). Evaporate the solvent in vacuo to yield 1.01 g yellow oil. Purify by silica gel chromatography (CHCl3 :MeOH:NH4OH/100:10:1) to yield 740 mg (80%) yellow oil which crystallizes. Purify further by silica gel chromatography (50% methanol/methylene chloride) to yield 79 mg of the title compound as a white solid; mp 44°-45° C.

Workup

  1. customPartition between 5N sodium hydroxide and ethyl ether
  2. customSeparate the organic phase
  3. extractionextract the aqueous phase with ethyl ether (2×25 mL)
  4. dry with materialCombine the organic phases and dry (MgSO4)
  5. customEvaporate the solvent in vacuo

Sources & evidence

ORD record
ord-aff57cf8c2c44bdcbcc8ecb00bd1bc68
Source dataset
uspto-grants-1994_09
Patent number
US05348964

Reaction notes

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