Triethylamine → HCID 86642664, compound

HRID 1644513Notes

Reaction equation

HRID 1644513 reaction equation
[CH2:1]([N:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][OH:17])[CH:11]([CH3:18])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>ClCCl.C(Cl)(Cl)Cl.CO>[CH3:33][S:34]([O:17][CH2:16][CH2:15][N:12]1[CH2:13][CH2:14][CH:9]([N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:10][CH:11]1[CH3:18])(=[O:36])=[O:35]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 62657Potassium Phosphate, TribasicHCID 66774573HCID 66774573, compound2×

Product 1

HCID 86642664HCID 86642664, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21584188Chloroform methanolSolvent

Procedure

A mixture 2-[4-(dibenzylamino)-2-methylpiperidin-1-yl]ethanol (Intermediate 216, 660 mg, 1.9 mmol) in dry dichloromethane (6 mL) and triethyl amine (0.375 mL, 2.7 mmol) was treated at 0° C. with methanesulfonyl chloride (0.175 mL, 8.4 mmol). After 45 minutes the reaction was complete by TLC (chloroform/methanol 6:1, rf 0.54). Potassium phosphate buffer (pH 7, 1M, 25 mL) was added, dichloromethane was removed under reduced pressure and it was extracted with ice cold ethyl acetate (2×100 mL) and dried over sodium sulfate. The solvent was removed under reduced pressure and the crude preparation of the mesylate was used without delay for the next step.

Workup

  1. customdichloromethane was removed under reduced pressure and it
  2. extractionwas extracted with ice cold ethyl acetate (2×100 mL)
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe crude preparation of the mesylate

Sources & evidence

ORD record
ord-6aebf2f0424942739ea06ef17a8dbeca
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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