1-Heptanethiol → HCID 85639082, compound

HRID 2226475Notes

Reaction equation

HRID 2226475 reaction equation
[O-]CC.[Na+].[Na].Cl.[Cl:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[CH2:16]([SH:23])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>C(O)C>[ClH:7].[CH2:16]([S:23][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 154221-HeptanethiolHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 2723922Sodium ethoxide3×HCID 5360545Sodium

Product 1

HCID 85639082HCID 85639082, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

Generate sodium ethoxide by carefully adding sodium metal (1.4 g, 60 mmol) to absolute ethanol (50 mL). Add 1/2 of the sodium ethoxide (30 mL) to a solution of N-(2-chloroethyl)-piperidine hydrochloride (5.0 g, 27.2 mmol) in absolute ethanol. Add the other 1/2 of the sodium ethoxide (30 mL) to a solution of heptyl mercaptan (4.6 mL, 30 mmol) in absolute ethanol. Mix the two and stir at room temperature overnight. Concentrate in vacuo, partition between water and ethyl acetate and separate the organic phase. Extract the aqueous phase with ethyl acetate (2×50 mL), combine the organic phases and dry (MgSO4). Evaporate the solvent in vacuo to yield 6.34 g yellow oil. Dissolve the oil in ethyl ether, filter and treat with anhydrous hydrochloric acid. Collect the resulting white solid by vacuum filtration (5.6 g) and recrystallize (ethyl acetate/isopropanol) to yield 3.12 g of the title compound as white crystals; mp 169°-70° C.

Workup

  1. additionMix the two
  2. concentrationConcentrate in vacuo
  3. custompartition between water and ethyl acetate
  4. customseparate the organic phase
  5. extractionExtract the aqueous phase with ethyl acetate (2×50 mL)
  6. dry with materialdry (MgSO4)
  7. customEvaporate the solvent in vacuo

Sources & evidence

ORD record
ord-0f118c7830f04177b07150c64c033331
Source dataset
uspto-grants-1994_09
Patent number
US05348964

Reaction notes

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