Triethylamine → 1-(4-Cyanophenyl)-4-mesyloxymethyl-piperidine

HRID 1757007Notes

Reaction equation

HRID 1757007 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][OH:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][O:16][S:25]([CH3:24])(=[O:27])=[O:26])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 193912964-(4-(Hydroxymethyl)piperidin-1-yl)benzonitrile

Product 1

HCID 193912701-(4-Cyanophenyl)-4-mesyloxymethyl-piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.5 g of 1-(4-cyanophenyl)-4-hydroxymethyl-piperidine and 5.16 g of triethylamine in 150 ml of methylene chloride, 5.84 g of methanesulphonic acid chloride are slowly added dropwise at ambient temperature and with stirring. After it has all been added the mixture is left to stand overnight and the solvent is removed under reduced pressure. The residue is chromatographed with methylene chloride/methanol (50:1) over silica gel. Yield: 6.95 g (93% of theory), Mass spectrum: (M+H)+ =295

Workup

  1. additionall been added the mixture
  2. waitis left
  3. customthe solvent is removed under reduced pressure
  4. customThe residue is chromatographed with methylene chloride/methanol (50:1) over silica gel

Sources & evidence

ORD record
ord-70d7912ec63f40edb04c7797831045c4
Source dataset
uspto-grants-1995_08
Patent number
US05442064

Reaction notes

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