Methyl iodide → HCID 11167382, compound

HRID 1786288Notes

Reaction equation

HRID 1786288 reaction equation
[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH2:4][C:5](=[CH:10][C:11]([C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)([C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)[OH:12])[CH2:6]2.C[I:24].[C:25]([O-])([O-])=O.[K+].[K+]>CC#N.C(Cl)Cl>[I-:24].[OH:12][C:11]([C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)([C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)[CH:10]=[C:5]1[CH2:4][CH:3]2[N+:2]([CH3:25])([CH3:1])[CH:7]([CH2:8][CH2:9]2)[CH2:6]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 11484351HCID 11484351, compound

Product 1

HCID 11167382HCID 11167382, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-1,1-di-thiophen-2-yl-ethanol (10 mg, 0.03 mmol) in CH3CN (1 mL) and CH2Cl2 (0.5 mL) was mixed with methyliodide (0.038 mL, 0.6 mmol) and K2CO3 (0.1 g, 0.7 mmol). The mixture was stirred overnight at r.t. and filtered. Separation via a reverse-phase HPLC then afforded the title compound (10 mg, 96%): LCMS (ES) m/z 346 (M+H)+; 1H-NMR(CDCl3) δ 1.28 (m, 1H), 2.04 (m, 2H), 2.29 (m, 1H), 2.51 (m, 2H), 2.64 (m, 1H), 3.30 (s, 6H), 4.07 (m, 1H), 4.38 (m, 1H), 5.93 (s, 1H), 6.62 (m, 1H), 6.85 (m, 1H), 6.98 (m, 1H), 7.03 (m, 1H), 7.11 (m, 1H), 7.46 (m, 1H).

Workup

  1. filtrationfiltered
  2. customSeparation via a reverse-phase

Sources & evidence

ORD record
ord-9dae07e19343494ca2fe90fa06300d88
Source dataset
uspto-grants-2009_03
Patent number
US07507747B2

Reaction notes

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