Triethylamine → HCID 4362638, compound

HRID 1291199Notes

Reaction equation

HRID 1291199 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl>[CH3:22][S:23]([O:14][CH:11]1[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][CH2:10]1)(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 784611-Benzylpiperidin-4-ol

Product 1

HCID 4362638HCID 4362638, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.0 g (0.01045 mol) of 1-benzyl-4-hydroxypiperidine were dissolved in 20 ml of dichlormethane and 5.1 ml (0.0366 mol) of triethylamine, cooled to 00 and treated with a solution of 1 ml (0.01255 mol) of methanesulfonyl chloride in 5 ml of dichloromethane. The mixture was stirred at 0° for 1/2 hr. Then, 10ml of 1N aqueous HCI were added, the mixture was stirred for 5 min. and the organic phase was washed with 1N aqueous HCI, with saturated bicarbonate solution and saturated sodium chloride solution and dried over magnesium sulfate. 0.97 g (35%) of 1-benzylpiperidin-4-yl methanesulfonate was obtained as yellow crystals. MS: me/e=270 (C13 H20NO3S+).

Workup

  1. additionThen, 10ml of 1N aqueous HCI were added
  2. stirringthe mixture was stirred for 5 min.
  3. washthe organic phase was washed with 1N aqueous HCI, with saturated bicarbonate solution and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-b9352594ab9342cba5ad59d68495edcf
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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