Triethylamine → HCID 18919744, compound

HRID 1291124Notes

Reaction equation

HRID 1291124 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].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>>[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH:35]1[CH2:34][CH2:33][N:32]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:37][CH2:36]1)=[O:5]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 118972,4-Dimethylbenzoic acidHCID 65578Oxalyl chlorideHCID 784611-Benzylpiperidin-4-ol

Product 1

HCID 18919744HCID 18919744, compoundYield 83%

Procedure

0.45 g (0.003 mol) of 2,4-dimethylbenzoic acid were boiled under reflux in 5.2 ml (0.06 mol) of oxalyl chloride for 3 hrs. After removal of the excess oxalyl chloride the mixture was concentrated twice with 5 ml of toluene each time. The residue was dissolved in 20 ml of toluene, treated with 0.74 ml (0.0053 mol) of triethylamine and 0.574 g (0.003 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). 0.805 g (83%) of 1-benzyl-piperidin-4-yi 2,4-dimethyl-benzoate was obtained as a yellow oil. MS: me/e=324 (C21H26NO2 +).

Workup

  1. customAfter removal of the excess oxalyl chloride the mixture
  2. concentrationwas concentrated twice with 5 ml of toluene each time
  3. dissolutionThe residue was dissolved in 20 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-c4e9cf0491fd4c5db1b8405ec44bcc1b
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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