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Triethylamine → 4-Aminomethyl-N-[3-(3,5-bis(trifluoromethyl)benzyloxy)-2-phenylpropyl]benzamide hydrochloride

HRID 548206
Notes
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Reaction equation

HRID 548206 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]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 204431481,4-Dioxane hydrochlorideHCID 866240403-(3,5-Bis(trifluoromethyl)benzyloxy)-2-phenylpropylamine hydrochlorideHCID 866240544-amino-N-[3-(3,5-bis(trifluoromethyl)benzyloxy)-2-ph enylpropyl]benzamide hydrochloride

Product 1

HCID 866240564-Aminomethyl-N-[3-(3,5-bis(trifluoromethyl)benzyloxy)-2-phenylpropyl]benzamide hydrochlorideYield 59%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07939552B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes