Triethylamine → HCID 18919872, compound

HRID 1291071Notes

Reaction equation

HRID 1291071 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7])([O-:3])=[O:2].[CH2:13]([N:20]1[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([O:26][CH:23]1[CH2:24][CH2:25][N:20]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:21][CH2:22]1)=[O:7])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 118752-Nitrobenzoyl chlorideHCID 784611-Benzylpiperidin-4-ol

Product 1

HCID 18919872HCID 18919872, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.55 g (0.00837 mol) of 2-nitro-benzoyl chloride were dissolved in 70 ml of toluene and treated with 2.0 g (0.0104 mol) of 1-benzyl-4-hydroxypiperidine and 2.6 ml (0.0184 mol) of triethylamine. After boiling under reflux for 18 hrs. the suspension was filtered, the filtrate was concentrated and the residue was chromatographed over silica gel with ethyl acetate/hexane (1:2->1:1) as the eluent. 1.7 g (60%) of 1-benzyl-piperidin-4-yl 2-nitro-benzoate were obtained as yellow crystals; m.p. 98°-99°.

Workup

  1. temperatureunder reflux for 18 hrs
  2. filtrationthe suspension was filtered
  3. concentrationthe filtrate was concentrated
  4. customthe residue was chromatographed over silica gel with ethyl acetate/hexane (1:2->1:1) as the eluent

Sources & evidence

ORD record
ord-2c6f0cf2189c496ca7cf686257f7edb0
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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