Water → 1-(4-Pyrimidinyl)-4-methyl-4-(ethoxycarbonyl)piperidine

HRID 2289539Notes

Reaction equation

HRID 2289539 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH2:8]2)=[N:3][CH:2]=1.[CH:18]([N-]C(C)C)(C)C.[Li+].IC.O>O1CCCC1>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][C:10]([CH3:18])([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH2:8]2)=[N:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 227219571-(4-Pyrimidinyl)-4-(ethoxycarbonyl)piperidine

Product 1

HCID 186980361-(4-Pyrimidinyl)-4-methyl-4-(ethoxycarbonyl)piperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-(4-pyrimidinyl)-4-(ethoxycarbonyl)piperidine (400 mg) in 4 ml tetrahydrofuran was cooled to -70° C and treated with a solution of lithium diisopropylamide (1.0 ml in THF), under an argon atmosphere. After stirring 1.5 hours 1.2 ml of a solution of 1 ml iodomethane in 10 ml THF was added and reaction mixture left to reach room temperature overnight. Water added and extracted twice with ethyl acetate. Organic extract washed with brine and dried over magnesium sulphate, filtered and evaporated to give 1-(4-pyrimidinyl)-4-methyl-4-(ethoxycarbonyl)piperidine (370 mg) as an oil; NMR (CDCl3): 1.24 (s, 3H), 1.28 (t, 3H), 1.38-1.51 (m,2H), 2.14-2.26 (m, 2H), 3.12-3.26 (m, 2H), 4.03-4.14 (m, 2H), 4.2(q,2H), 6.5 (dd, 1H), 8.17 (d. 1H), 8.57 (s, 1H)

Workup

  1. additionwas added
  2. customreaction mixture
  3. waitleft
  4. extractionextracted twice with ethyl acetate
  5. extractionOrganic extract
  6. washwashed with brine
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-7cee8ec630e2401198303bb37e025e2a
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

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