4-Hydroxybenzoic Acid → N-[3-(3,5-bis(trifluoromethyl)benzyloxy)-2-phenylpropyl]-4-hydroxybenzamide
Reaction equation
[Cl-].C([N+]1C=CC(C(=O)NCC(C2C=CC=CC=2)COCC2C=CC(C(F)(F)F)=C(C(F)(F)F)C=2)=CC=1)C1C=CC=CC=1.[OH:43][C:44]1[CH:52]=[CH:51][C:47]([C:48]([OH:50])=O)=[CH:46][CH:45]=1.Cl.[F:54][C:55]([F:79])([F:78])[C:56]1[CH:57]=[C:58]([CH:71]=[C:72]([C:74]([F:77])([F:76])[F:75])[CH:73]=1)[CH2:59][O:60][CH2:61][CH:62]([C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)[CH2:63][NH2:64].C(N(CC)CC)C.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[F:54][C:55]([F:78])([F:79])[C:56]1[CH:57]=[C:58]([CH:71]=[C:72]([C:74]([F:75])([F:77])[F:76])[CH:73]=1)[CH2:59][O:60][CH2:61][CH:62]([C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)[CH2:63][NH:64][C:48](=[O:50])[C:47]1[CH:46]=[CH:45][C:44]([OH:43])=[CH:52][CH:51]=1Participants
7
Reactant 5
HCID 1354-Hydroxybenzoic Acid
HCID 8471Triethylamine
HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride
HCID 866240403-(3,5-Bis(trifluoromethyl)benzyloxy)-2-phenylpropylamine hydrochloride
HCID 866240421-Benzyl-4-[3-(3,4-bis(trifluoromethyl)-benzyloxy)-2-p henylpropylcarbamoyl]pyridinium chlorideProduct 1
Reagents, catalysts & solvents 1
Procedure
In the same manner as in the case of synthesis of Compound 30, a residue was given from 4-hydroxybenzoic acid (0.33 g, 2.4 mmol), the compound produced in Example 17 (0.83 g, 2.0 mmol), triethylamine (0.28 mL, 2.0 mmol), WSC.HCl (0.46 g, 2.4 mmol) and CH2Cl2 (10 mL). The oily residue was crystallized from petroleum ether to give the Compound 56 (0.61 g, 61%).
Workup
- customThe oily residue was crystallized from petroleum ether
Sources & evidence
- ORD record
- ord-208da2d06529414e8797a1e9beff0c0a
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07939552B2
Reaction notes
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