Triethylamine → Methanesulfonic Acid Trans-{1-[2-(4-fluorophenyl)ethyl]-4-methylpiperidin-3-ylmethyl} Ester

HRID 896538Notes

Reaction equation

HRID 896538 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][C@@H:13]([CH3:16])[C@H:12]([CH2:17][OH:18])[CH2:11]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][C@@H:13]([CH3:16])[C@H:12]([CH2:17][O:18][S:27]([CH3:26])(=[O:29])=[O:28])[CH2:11]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69736259trans-{1-[2-(4-Fluorophenyl)ethyl]-4-methylpiperidin-3-yl}-methanol

Product 1

HCID 86591720Methanesulfonic Acid Trans-{1-[2-(4-fluorophenyl)ethyl]-4-methylpiperidin-3-ylmethyl} Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of trans-{1-[2-(4-fluorophenyl)ethyl]-4-methylpiperidin-3-yl}-methanol (251 mg, 1.0 mmol) in dichloromethane (10 mL) was treated with triethylamine (280 μL, 2.0 mmol) and stirred on an ice-acetone bath. Methanesulfonyl chloride (85 μL, 1.1 mmol) was added dropwise, and the resulting solution was stirred at room temperature for 1.5 hours. The solution was concentrated under vacuum, and the residue was taken up in ethyl acetate and filtered. The filtrate was concentrated under vacuum to provide an orange gum (342 mg, quantitative) which was used without further purification. 1H NMR (300 MHz, CDCl3) δ7.16 (m, 2H), 6.98 (t, J=9 Hz, 2H), 4.30 (dd, J=10, 3 Hz, 1H), 4.18 (dd, J=10, 7 Hz, 1H), 3.13 (dm, J=10 Hz, 1H), 3.02 (s+m, 4H), 2.83 (m, 2H), 2.66 (m, 2H), 2.07 (m, 2H), 1.76 (m, 2H), 1.43 (m, 2H), 1.02 (d, J=6, 3H).

Workup

  1. stirringthe resulting solution was stirred at room temperature for 1.5 hours
  2. concentrationThe solution was concentrated under vacuum
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under vacuum
  5. customto provide an orange gum (342 mg, quantitative) which
  6. customwas used without further purification

Sources & evidence

ORD record
ord-e0191e8edecd4c6abcbd3c4a3bb86743
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

Loading…