Triethylamine → HCID 18919843, compound

HRID 1291069Notes

Reaction equation

HRID 1291069 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](Cl)=[O:8])([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:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([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:8])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8495Benzoyl chloride, 3-nitro-HCID 784611-Benzylpiperidin-4-ol

Product 1

HCID 18919843HCID 18919843, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.388 g (0.0021 mol) of 3-nitro-benzoyl chloride were dissolved in 20 ml of toluene under argon and treated while stirring with 0.5 g (0.0026 mol) of 1-benzyl-4-hydroxy-piperidine and 0.643 ml (0.0046 mol) of triethylamine. After boiling at reflux for 2 hrs. the suspension was filtered and the filtrate was completely freed from solvent. The residue was chromatographed over silica gel with ethyl acetate/hexane 1:2 as the eluent. 0.65 g (92%) of 1-benzyl-piperidin-4-yl 3-nitro-benzoate was obtained as a yellow oil. MS: mele (% basic peak)=340 (C19H20 N2O4+, 27), 263 (25), 173 (36.5), 150 (14.5), 91 (100), 82 (100).

Workup

  1. additiontreated
  2. temperatureat reflux for 2 hrs
  3. filtrationthe suspension was filtered
  4. customThe residue was chromatographed over silica gel with ethyl acetate/hexane 1:2 as the eluent

Sources & evidence

ORD record
ord-0a237eb2aec84b23976a2c3209d304ec
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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