Triethylamine → HCID 23103400, compound

HRID 499194Notes

Reaction equation

HRID 499194 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.[Cl:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:24]=1[C:25](Cl)=[O:26]>ClCCl>[NH2:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][N:12]([C:25]([C:24]3[C:23]([Cl:22])=[CH:31][CH:30]=[CH:29][C:28]=3[Cl:32])=[O:26])[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 783922,6-Dichlorobenzoyl chlorideHCID 23103412Benzenamine, 3-(4-piperidinyl)-, hydrochloride (1:?)

Product 1

HCID 23103400HCID 23103400, compoundYield 46.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To an ice-cooled solution of 4-(3-aminophenyl)-piperidine hydrochloride (250.2 mg, 1.0 mmol) and triethylamine (1 mL) in dichloromethane (6 mL) is added 2,6-dichlorobenzoic chloride (0.15 mL, 1.0 mmol). The reaction mixture is stirred at 0° C. for 6 hours. After removal of solvent, the residue is purified on a silica gel chromatography with ethyl acetate-hexanes to provide a white solid (163.9 mg, 46.9% yield, ES+(m/z) 349.1 [M+H]).

Workup

  1. customAfter removal of solvent
  2. customthe residue is purified on a silica gel chromatography with ethyl acetate-hexanes
  3. customto provide a white solid (163.9 mg, 46.9% yield, ES+(m/z) 349.1 [M+H])

Sources & evidence

ORD record
ord-e03e022da06247ffab33a5b81591c54f
Source dataset
uspto-grants-2010_08
Patent number
US07767674B2

Reaction notes

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