Benzoyl chloride → HCID 18919752, compound

HRID 1291168Notes

Reaction equation

HRID 1291168 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][CH2:10]2)=[CH:6][CH:5]=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:15][CH:12]1[CH2:11][CH2:10][N:9]([CH2:8][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:17][CH:16]=2)[CH2:14][CH2:13]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 765041HCID 765041, compound

Product 1

HCID 18919752HCID 18919752, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.3 g (0.00127mol) of 1-(4-nitro-benzyl)-piperidin-4-ol and 0.356 ml (0.00254 mol) of triethylamine were dissolved in 10 ml of toluene, treated with 0.177 ml (0.0015 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). 0.335 g (78%) of 1-(4-nitro-benzyl)-piperidin-4-yl benzoate was obtained as yellow crystals. MS: me/e (% basic peak)=340 (C19H20O4+, 3.5), 235 (5), 218 (41), 105 (26), 82 (100).

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-2acf412163854f46baa96262a751e875
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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