Triethylamine → 1-Benzyl-piperidin-4-yl 4-nitro-benzoate

HRID 1291073Notes

Reaction equation

HRID 1291073 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.[N+:22]([C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1)([O-:24])=[O:23]>C1(C)C=CC=CC=1>[N+:22]([C:25]1[CH:26]=[CH:27][C:28]([C:29]([O:14][CH:11]2[CH2:12][CH2:13][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9][CH2:10]2)=[O:30])=[CH:32][CH:33]=1)([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 784611-Benzylpiperidin-4-ol

Product 1

HCID 189198161-Benzyl-piperidin-4-yl 4-nitro-benzoateYield 106.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.5 g (0.00216 mol) of 1-benzyl-4-hydroxypiperidine and 0.64 ml (0.0046 mol) of triethylamine were dissolved in 20 ml of toluene, treated with 0.5 g (0.0027 mol) of 4-nitro-benzoyl chloride and boiled at reflux for 6 hrs. The suspension was filtered, the filtrate was concentrated and the residue was chromatographed over silica gel with ethyl acetatelhexane (1:3) as the eluent. 0.78 g (85%) of 1-benzyl-piperidin-4-yl 4-nitro-benzoate was obtained as yellow crystals; m.p. 87°-89°.

Workup

  1. temperatureat reflux for 6 hrs
  2. filtrationThe suspension was filtered
  3. concentrationthe filtrate was concentrated
  4. customthe residue was chromatographed over silica gel with ethyl acetatelhexane (1:3) as the eluent

Sources & evidence

ORD record
ord-2eb1e9d417994a7ebcba4774e1006ae2
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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