Iodoethane → HCID 67820205, compound

HRID 1729471Notes

Reaction equation

HRID 1729471 reaction equation
C(OC([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][CH3:30])[C@H:9]1[C@@H:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[NH:13][C:12](=[O:21])[CH2:11][CH2:10]1)=O)(C)(C)C.[CH3:31][C:32](C)([O-])C.[K+].C(I)C>C1COCC1>[CH2:31]([N:13]1[C@H:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@H:9]([NH:8][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH3:30])[CH2:10][CH2:11][C:12]1=[O:21])[CH3:32]

Participants

5

Reactant 3

HCID 6340Iodoethane2×HCID 23665647Potassium tert-butoxide2×HCID 67820261HCID 67820261, compound

Product 1

HCID 67820205HCID 67820205, compoundYield 103.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere in a round-bottom flask were placed 50 ml (0.12 mmol) of cis-5-(N-tert-butoxycarbonyl-2-methoxybenzylamino)-2-oxo-6-phenylpiperidine and 0.2 mL of THF. To the system were added 13.5 mg (0.12 mmol) of potassium tert-butoxide and 20 μL (0.24 mmol) of ethyl iodide. The reaction mixture was stirred at room temperature for 3 hours (during this period, additional potassium tert-butoxide (13.5 mg) and ethyl iodide (20 μL) were added to the system). The mixture was partitioned between methylene chloride and aqueous sodium bicarbonate, the layers were separated and the aqueous phase was extracted with three portions of methylene chloride. The combined organic fractions were dried (sodium sulfate) and concentrated with a rotary evaporator. The crude material was purified by flash column chromatography using 3:97 methanol/chloroform as the eluant to obtain 42 mg of cis-N-ethyl-5-(2-methoxybenzylamino)-2-oxo-6-phenylpiperidine.

Workup

  1. customUnder a nitrogen atmosphere in a round-bottom flask were placed
  2. customThe mixture was partitioned between methylene chloride and aqueous sodium bicarbonate
  3. customthe layers were separated
  4. extractionthe aqueous phase was extracted with three portions of methylene chloride
  5. dry with materialThe combined organic fractions were dried (sodium sulfate)
  6. concentrationconcentrated with a rotary evaporator
  7. customThe crude material was purified by flash column chromatography

Sources & evidence

ORD record
ord-3fef08bbe2464b8e97016ad0d8b183c8
Source dataset
uspto-grants-1994_07
Patent number
US05332817

Reaction notes

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