Triethylamine → HCID 18919829, compound

HRID 1291164Notes

Reaction equation

HRID 1291164 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)([O-:3])=[O:2].C(N(CC)CC)C.[CH3:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1>C1(C)C=CC=CC=1>[CH3:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([O:14][CH:11]2[CH2:10][CH2:9][N:8]([CH2:7][C:6]3[CH:15]=[CH:16][CH:17]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[CH2:13][CH2:12]2)=[O:31])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 765448HCID 765448, compound

Product 1

HCID 18919829HCID 18919829, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.65 g (0.00275 mol) of 1-(3-nitro-benzyl)-piperidin-4-ol and 1.9 ml (0.0136 mol) of triethylamine were dissolved in 27.5 ml of toluene, treated with 1.09 ml (0.00825 mol) of 4-methyl-benzoyl chloride and boiled at reflux for 18 hrs. The reaction mixture was concentrated and the residue was chromatographed over silica gel with ethyl acetate/hexane (1:3). 0.715 g (73%) of 1-(3-nitro-benzyl)-piperidin-4-yl 4-methyl-benzoate was obtained as yellow crystals; m.p. 90°-93°.

Workup

  1. temperatureat reflux for 18 hrs
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was chromatographed over silica gel with ethyl acetate/hexane (1:3)

Sources & evidence

ORD record
ord-fd25982ca535471499a005e77956d885
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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