Hydrochloric Acid → HCID 85639286, compound

HRID 2226462Notes

Reaction equation

HRID 2226462 reaction equation
[CH2:1]([S:6][CH2:7][CH2:8][CH2:9][Cl:10])[CH2:2][CH:3]([CH3:5])[CH3:4].[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.Cl>C(OCC)C>[ClH:10].[CH2:1]([S:6][CH2:7][CH2:8][CH2:9][N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 18965257HCID 18965257, compound

Product 1

HCID 85639286HCID 85639286, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
125 °C

Procedure

Mix 3-chloropropyl isopentyl sulfide (1.0 g, 5.5 mmol) and piperidine (3.3 mL, 33 mmol) and heat at 125° C. for 2 hours. Cool to room temperature and partition between 50% sodium hydroxide and ethyl ether. Separate the organic phase, wash the aqueous phase with ethyl ether (2×30 mL), combine the organic phases and dry (MgSO4). Evaporate the solvent in vacuo to yield 1.12 g (89%). Dissolve the product (1.0 g) in ethyl ether (100 mL) and treat with anhydrous hydrochloric acid. Collect the resulting yellow solid by vacuum filtration, recrystallize (ethyl acetate) and dry to yield 0.723 g of the title compound as white crystals; mp 155°-8° C. 438E-83

Workup

  1. temperatureCool to room temperature
  2. custompartition between 50% sodium hydroxide and ethyl ether
  3. customSeparate the organic phase
  4. washwash the aqueous phase with ethyl ether (2×30 mL)
  5. dry with materialdry (MgSO4)
  6. customEvaporate the solvent in vacuo
  7. customto yield 1.12 g (89%)
  8. customCollect the resulting yellow solid
  9. filtrationby vacuum filtration
  10. customrecrystallize (ethyl acetate)
  11. customdry

Sources & evidence

ORD record
ord-a21dc9a2268e491aa03005ca907743e4
Source dataset
uspto-grants-1994_09
Patent number
US05348964

Reaction notes

Loading…