Triethylamine → HCID 86642664, compound

HRID 255380Notes

Reaction equation

HRID 255380 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-1fc8661ad50f4108bfb48e22d04e1af1
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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