Methyl iodide → HCID 178501214, compound

HRID 2279340Notes

Reaction equation

HRID 2279340 reaction equation
[CH3:1]C([O-])(C)C.[K+].[CH3:7][O:8][C:9]([C@H:11]1[CH2:16][CH2:15][C@H:14]([NH:17][CH2:18][C:19]2[CH:28]=[CH:27][C:22]3[O:23][CH2:24][CH2:25][O:26][C:21]=3[CH:20]=2)[CH2:13][CH2:12]1)=[O:10].CI>CN(C)C=O>[CH3:7][O:8][C:9]([C@H:11]1[CH2:16][CH2:15][C@H:14]([N:17]([CH2:18][C:19]2[CH:28]=[CH:27][C:22]3[O:23][CH2:24][CH2:25][O:26][C:21]=3[CH:20]=2)[CH3:1])[CH2:13][CH2:12]1)=[O:10]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 23665647Potassium tert-butoxideHCID 178501211HCID 178501211, compound

Product 1

HCID 178501214HCID 178501214, compoundYield 1,616%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium tert-butylate (35 mg, 0.31 mmol, 1.0 eq) is added at room temperature to a stirred solution of trans-4-[(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-amino]-cyclohexanecarboxylic acid methyl ester (100 mg, 0.31 mmol, 1.0 eq) in N,N-dimethylformamide (4 mL), followed by methyl iodide (10 μL, 0.16 mmol, 0.5 eq). After 15 hours stirring at room temperature methyl iodide (10 μL, 0.16 mmol, 0.5 eq) is added again. After 4 hours stirring at room temperature, solvent is evaporated and the residue is extracted with ethyl acetate (3×5 mL) and water (5 mL). The combined organic layers are washed with brine (5 mL), dried over sodium sulfate, filtered and concentrated to afford trans-4-[(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-methyl-amino]-cyclohexanecarboxylic acid methyl ester as a brown oil (1.60 g, 98% yield).

Workup

  1. additionis added again
  2. customsolvent is evaporated
  3. extractionthe residue is extracted with ethyl acetate (3×5 mL) and water (5 mL)
  4. washThe combined organic layers are washed with brine (5 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0e29bdaab4b044139e3bb5050ed5e164
Source dataset
uspto-grants-2015_09
Patent number
US09133219B2

Reaction notes

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