Triethylamine → HCID 18919746, compound

HRID 1291125Notes

Reaction equation

HRID 1291125 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[CH2:25]([N:32]1[CH2:37][CH2:36][CH:35](O)[CH2:34][CH2:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH:35]2[CH2:34][CH2:33][N:32]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:37][CH2:36]2)=[O:7])=[C:4]([CH3:11])[CH:3]=1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 784611-Benzylpiperidin-4-olHCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 18919746HCID 18919746, compoundYield 59%

Procedure

2.0 g (0.0093 mol) of 4-bromo-2-methylbenzoic acid were boiled under reflux in 15 ml (0.175 mol) of oxalyl chloride for 3 hrs. After removal of the excess oxalyl chloride the mixture was concentrated twice with 10 ml of toluene each time. The residue was dissolved in 15 ml of toluene, treated with 2.33 ml (0.01675 mol) of triethylamine and 2.67 g (0.01395 mol) of 1-benzyl-4-hydroxypiperidine and boiled at reflux for 18 hrs. After removal of the solvent the residue was chromatographed on silica gel with ethyl acetate/hexane (1:3). 2.12 g (59%) of 1-benzyl-piperidin-4-yl 4-bromo-2-methyl-benzoate were obtained as a yellow oil.

Workup

  1. customAfter removal of the excess oxalyl chloride the mixture
  2. concentrationwas concentrated twice with 10 ml of toluene each time
  3. dissolutionThe residue was dissolved in 15 ml of toluene
  4. temperatureat reflux for 18 hrs
  5. customAfter removal of the solvent the residue
  6. customwas chromatographed on silica gel with ethyl acetate/hexane (1:3)

Sources & evidence

ORD record
ord-f27f5cf57b9a4f9699f65f3df6819c63
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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