Triethylamine → 4-Aminomethyl-N-[3-(3,5-bis(trifluoromethyl)benzyloxy)-2-phenylpropyl]benzamide hydrochloride
Reaction equation
[ClH:1].FC(F)(F)C1C=C(C=C(C(F)(F)F)C=1)COCC(C1C=CC=CC=1)[CH2:11][NH2:12].C(N(CC)CC)C.CCN=C=NCCCN(C)C.Cl.Cl.N[C:49]1[CH:82]=[CH:81][C:52]([C:53]([NH:55][CH2:56][CH:57]([C:75]2[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=2)[CH2:58][O:59][CH2:60][C:61]2[CH:66]=[C:65]([C:67]([F:70])([F:69])[F:68])[CH:64]=[C:63]([C:71]([F:74])([F:73])[F:72])[CH:62]=2)=[O:54])=[CH:51][CH:50]=1.Cl.O1CCOCC1>O1CCOCC1.C(Cl)Cl>[ClH:1].[NH2:12][CH2:11][C:49]1[CH:50]=[CH:51][C:52]([C:53]([NH:55][CH2:56][CH:57]([C:75]2[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=2)[CH2:58][O:59][CH2:60][C:61]2[CH:66]=[C:65]([C:67]([F:70])([F:69])[F:68])[CH:64]=[C:63]([C:71]([F:74])([F:72])[F:73])[CH:62]=2)=[O:54])=[CH:81][CH:82]=1Participants
8
Reactant 5
HCID 8471Triethylamine
HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride
HCID 204431481,4-Dioxane hydrochloride
HCID 866240403-(3,5-Bis(trifluoromethyl)benzyloxy)-2-phenylpropylamine hydrochloride
HCID 866240544-amino-N-[3-(3,5-bis(trifluoromethyl)benzyloxy)-2-ph enylpropyl]benzamide hydrochlorideProduct 1
Reagents, catalysts & solvents 2
Procedure
Compound 69 (1.05 g, 86%) was produced as an oily product from 4-tert-butoxycarbonylaminomethylbenzoic acid (0.60 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) according to the same manner as in Example 30. In the same manner as in the case of synthesis of Compound 61, Compound 63 (0.55 g, 59%) was produced from Compound 69 (1.04 g, 1.7 mmol), 4 mol/L hydrogen chloride/dioxane (2.6 mL) and dioxane (2.6 mL).
Sources & evidence
- ORD record
- ord-eab00d1aefbd44a9bd40a96bfd23fb09
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07939552B2
Reaction notes
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