Iodoethane → HCID 44554169, compound

HRID 1894273Notes

Reaction equation

HRID 1894273 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C@@H:11]([N:18]1[N:22]=[N:21][CH:20]=[N:19]1)[C@H:12]1[CH2:17][CH2:16][CH2:15][NH:14][CH2:13]1.[CH2:23](N(CC)CC)[CH3:24].ICC>C(#N)C.C(OCC)(=O)C>[CH2:23]([N:14]1[CH2:15][CH2:16][CH2:17][C@H:12]([C@@H:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[N:18]2[N:22]=[N:21][CH:20]=[N:19]2)[CH2:13]1)[CH3:24]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 8471TriethylamineHCID 44555334HCID 44555334, compound

Product 1

HCID 44554169HCID 44554169, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

(3S)-3-[(S)-naphthalen-2-yl(2H-tetrazol-2-yl)methyl]piperidine (2.0 mmol) from Example 2 was dissolved in acetonitrile and the solution was treated with triethylamine (3.0 mmol) at room temperature. To this solution was added iodoethane in acetonitrile slowly and the solution was warmed up to 40° C. After the completion of the reaction, the reaction mixture was diluted with ethyl acetate, washed with 5% aq NaOH, water, brine, and dried over MgSO4. After concentration, the crude product was purified by flash column chromatography with a 10% Methanol in dichloromethane to afford (3S)-1-ethyl-3-[(S)-naphthalen-2-yl(2H-tetrazol-2-yl)methyl]piperidine.

Workup

  1. customAfter the completion of the reaction
  2. washwashed with 5% aq NaOH, water, brine
  3. dry with materialdried over MgSO4
  4. concentrationAfter concentration
  5. customthe crude product was purified by flash column chromatography with a 10% Methanol in dichloromethane

Sources & evidence

ORD record
ord-058cbae120924a6e90881b9ea6ec8f19
Source dataset
uspto-grants-2013_08
Patent number
US08513285B2

Reaction notes

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