Triethylamine → HCID 54537902, compound

HRID 897255Notes

Reaction equation

HRID 897255 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][OH:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl>[N:1]1([CH2:7][CH2:8][CH2:9][O:10][S:19]([CH3:18])(=[O:21])=[O:20])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66032Piperidine-1-propanol

Product 1

HCID 54537902HCID 54537902, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 20 mL scintillation vial equipped with a stirring bar and a septum screw cap, a solution of 3-piperidin-1-yl-propan-1-ol (0.500 g, 3.49 mmol) in DCM (5 mL) was cooled down to 0° C. Then, triethylamine (10 eq.) was added to the vial via a syringe followed by a solution of methanesulfonyl chloride (5 eq.) in DCM (1 mL). The resulting reaction mixture was allowed to slowly warm up to room temperature and stirring was maintained for additional 2 h. The volatiles were removed in vacuo and the resulting crude methanesulfonic acid 3-piperidin-1-yl-propyl ester was used in the next step of the synthesis without further purification (the material was found to contain 30% of the title compound by weight according to 1H NMR).

Workup

  1. customIn a 20 mL scintillation vial equipped with a stirring bar
  2. customa septum screw cap
  3. customThe resulting reaction mixture
  4. temperaturewas maintained for additional 2 h
  5. customThe volatiles were removed in vacuo
  6. customthe resulting crude methanesulfonic acid 3-piperidin-1-yl-propyl ester was used in the next step of the synthesis without further purification (the material

Sources & evidence

ORD record
ord-4fa947aecc204886ae84d96a323bc39f
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Reaction notes

Loading…