Acetonitrile → HCID 86680288, compound

HRID 2202596Notes

Reaction equation

HRID 2202596 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:10][CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:5][CH:4]=1.Cl[CH2:24][C:25]1[CH:26]=[C:27]([CH:33]=[CH:34][N:35]=1)[C:28]([O:30][CH2:31][CH3:32])=[O:29].C(#N)C.C(N(CC)CC)C>O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:10][CH:11]2[CH2:12][CH2:13][N:14]([CH2:24][C:25]3[CH:26]=[C:27]([CH:33]=[CH:34][N:35]=3)[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:15][CH2:16]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 10402376HCID 10402376, compoundHCID 21471717Ethyl 2-(chloromethyl)-4-pyridinecarboxylate

Product 1

HCID 86680288HCID 86680288, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 297 mg of a known compound (±)-4-[(4-methoxyphenyl)phenylmethoxy]piperidine, 240 mg of a known compound ethyl 2-chloromethylisonicotinate, 2.3 mL of acetonitrile, and 0.28 mL of triethylamine was stirred overnight. The mixture was poured into salt water and extracted with ethyl acetate. The extract was washed with a saturated saline solution and dried over sodium sulfate. The solvent was distilled off, and then the residue was purified by p-TLC to give the title compound (309 mg (67%)).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with a saturated saline solution
  3. dry with materialdried over sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by p-TLC

Sources & evidence

ORD record
ord-b1969c6be60c46e9806b881e46229eeb
Source dataset
uspto-grants-2016_06
Patent number
US09365553B2

Reaction notes

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