Methyl iodide → HCID 23467197, compound

HRID 443424Notes

Reaction equation

HRID 443424 reaction equation
[H-].[Na+].[C:3]1([CH:9]2[CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][N:17]3[C:11]3([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[O:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.I[CH3:24]>O1CCCC1>[CH3:24][N:14]1[CH2:13][CH2:12][C:11]2([N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]3[CH:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[O:10]2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 23467217HCID 23467217, compound

Product 1

HCID 23467197HCID 23467197, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (1.2 g of a 50% dispersion in a mineral oil) is added in portions to a stirred solution of 5.4 g of hexahydro-1-phenylspiro[3H-oxazolo[3,4-a]pyridine-3,4'-piperidine] in 100 ml of tetrahydrofuran at 25° C. The mixture is stirred 0.5 hours under nitrogen and 5 g iodomethane in 10 ml of tetrahydrofuran is added dropwise. The mixture is stirred at 45° C. for 3 hours, filtered and the filtrate is evaporated in vacuo. The residue is dissolved in methylene dichloride, washed with water, dried over magnesium sulfate and the solvent is evaporated. The residue is crystallized from ethyl acetate to obtain the desired hexahydro-1'-methyl-1-phenylspiro[3H-oxazolo-[3,4-a]pyridine-3,4'-piperidine]; mp 157°-159° C.

Workup

  1. stirringThe mixture is stirred at 45° C. for 3 hours
  2. filtrationfiltered
  3. customthe filtrate is evaporated in vacuo
  4. dissolutionThe residue is dissolved in methylene dichloride
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent is evaporated
  8. customThe residue is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-4a9e31d0589a40b8ae8504cf3fb8065a
Source dataset
uspto-grants-1981_04
Patent number
US04260623

Reaction notes

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