Methanesulfonic Acid → HCID 66836129, compound

HRID 2404493Notes

Reaction equation

HRID 2404493 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([OH:19])[C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=1[OH:18].CS(O)(=O)=O.[CH3:25][N:26]1[CH2:31][CH2:30][CH:29](O)[CH2:28][CH2:27]1>ClCCCl.CN1CCCC1=O.O.ClCCl.[OH-].[Na+]>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([O:19][CH:29]1[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][CH2:28]1)[C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=1[OH:18]

Participants

9

Reactant 3

HCID 6395Methanesulfonic AcidHCID 660484-Piperidinol, 1-methyl-HCID 66836149HCID 66836149, compound

Product 1

HCID 66836129HCID 66836129, compound

Reagents, catalysts & solvents 5

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-[(1H-benzimidazol-2-yl)hydroxymethyl]-4-methylphenol (prepared according to procedure 561B) (360 mg), methanesulfonic acid (500 μL) and 1-methyl-4-piperidinol (500 mg) in 1,2-dichloroethane (20 mL) and N-methylpyrrolidinone (2 mL) is warmed at 90° C. for 2 h. After cooling at 0° C., the mixture is diluted with water and dichloromethane and concentrated sodium hydroxide slowly added up to pH 9. Organic phase is then dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography over silica gel (gradient dichloromethane/methanol/ammonia from 100/0/0.5 to 80/20/0.5) to afford 2-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-yloxy)methyl]-4-methylphenol, melting at 151° C.

Workup

  1. temperatureAfter cooling at 0° C.
  2. additionslowly added up to pH 9
  3. dry with materialOrganic phase is then dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by chromatography over silica gel (gradient dichloromethane/methanol/ammonia from 100/0/0.5 to 80/20/0.5)

Sources & evidence

ORD record
ord-1fcada0e2a27445ba05361f205082049
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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