Benzoyl chloride → HCID 18919779, compound

HRID 1291158Notes

Reaction equation

HRID 1291158 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[CH2:6][N:7]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]1)([O-:3])=[O:2].C(N(CC)CC)C.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1(C)C=CC=CC=1>[C:25]([O:13][CH:10]1[CH2:11][CH2:12][N:7]([CH2:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:8][CH2:9]1)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 7650181-[(2-Nitrophenyl)methyl]-4-piperidinol

Product 1

HCID 18919779HCID 18919779, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.5 g (0.00212 mol) of 1-(2-nitro-benzyl)-piperidin-4-ol and 0.595 ml (0.00424 mol) of triethylamine were dissolved in 15 ml of toluene, treated with 0.295 ml (0.00254 mol) of 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 :2). 0.484 g (75%) of 1-(2-nitro-benzyl)-piperidin-4-yl benzoate was obtained as a yellow oil. MS: me/e=341 (C19H21N2O4+).

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 :2)

Sources & evidence

ORD record
ord-9f771f1ae16f4a219f1cc6ce1ee241fa
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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