Iodoethane → HCID 86738911, compound

HRID 2166565Notes

Reaction equation

HRID 2166565 reaction equation
[C:1]1([CH:7]2[CH2:12][NH:11][CH2:10][CH:9]([OH:13])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][CH:15]1CCCN(C)C1(C)C.ICC>CO>[CH2:14]([N:11]1[CH2:12][C@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][C@H:9]([OH:13])[CH2:10]1)[CH3:15]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 12900715HCID 12900715, compoundHCID 187617721,2,2,3-Tetramethylpiperidine

Product 1

HCID 86738911HCID 86738911, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Phenyl-3-piperidinol (5.2 g), tetramethylpiperidine (8.3 ml) and iodoethane (1.97 ml) was stirred at room temperature in methanol (100 ml) for 48 hours. The methanol was removed under reduced pressure and excess 2 M NaOH added. The oil was extracted with ether and washed with brine. After drying (MgSO4) the ether was removed and the product crystallised affording, after recrystallisation from cyclohexane, 3.2 g of pure title compound which could be converted to the hydrochloride salt m.p. 182°-4° C.

Workup

  1. customThe methanol was removed under reduced pressure and excess 2 M NaOH
  2. additionadded
  3. extractionThe oil was extracted with ether
  4. washwashed with brine
  5. dry with materialAfter drying (MgSO4) the ether
  6. customwas removed
  7. customthe product crystallised
  8. customaffording
  9. customafter recrystallisation from cyclohexane, 3.2 g of pure title compound which

Sources & evidence

ORD record
ord-4ad1cd0e2f884c248e43bec97e166b20
Source dataset
uspto-grants-1983_06
Patent number
US04387230

Reaction notes

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