Methyl iodide → HCID 11515012, compound

HRID 1441946Notes

Reaction equation

HRID 1441946 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12](=[O:21])[NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[CH3:22]I.[OH-].[K+]>O1CCCC1>[CH3:22][N:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12](=[O:21])[NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 11507563HCID 11507563, compound

Product 1

HCID 11515012HCID 11515012, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
36 °C

Procedure

A mixture of heptyl-carbamic acid-1, 2, 3, 4-tetrahydro-quinolin-6-yl ester (0.58 g., 2 mmol), methyl iodide (0.224 ml, 3.6 mmol) and pulverized potassium hydroxide (0.16 g., 2 mmol) in dry tetrahydrofuran (10 ml) was stirred for 5 hours at room temperature (36° C.). The reaction mixture was concentrated under vaccum, diluted with water (5 ml), extracted with ether (3×5 ml), dried over sodium sulphate and the combined ether fractions were concentrated under vaccum. The residue was then chromatographed on deactivated silica gel (water: silica gel=12.88, v/w) using dichloromethane: hexane (20:80) as eluant to give 2n; yield: 0.36 g. (59.2%).

Workup

  1. concentrationThe reaction mixture was concentrated under vaccum
  2. additiondiluted with water (5 ml)
  3. extractionextracted with ether (3×5 ml)
  4. dry with materialdried over sodium sulphate
  5. concentrationthe combined ether fractions were concentrated under vaccum
  6. customThe residue was then chromatographed on deactivated silica gel (water

Sources & evidence

ORD record
ord-90546a4e407f44e490665091bcb47897
Source dataset
uspto-grants-2010_02
Patent number
US07655801B2

Reaction notes

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