Triethylamine → 4-amino-N-[3-(3,5-bis(trifluoromethyl)benzyloxy)-2-ph enylpropyl]benzamide hydrochloride

HRID 548205Notes

Reaction equation

HRID 548205 reaction equation
[ClH:1].[F:2][C:3]([F:27])([F:26])[C:4]1[CH:5]=[C:6]([CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1)[CH2:7][O:8][CH2:9][CH:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:11][NH2:12].[CH2:28](N(CC)CC)[CH3:29].CCN=C=N[CH2:40][CH2:41][CH2:42][N:43](C)C.Cl.Cl.[O:48]1[CH2:53][CH2:52]OCC1>O1CCOCC1.C(Cl)Cl>[ClH:1].[NH2:43][C:42]1[CH:41]=[CH:40][C:52]([C:53]([NH:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][O:8][CH2:7][C:6]2[CH:5]=[C:4]([C:3]([F:26])([F:27])[F:2])[CH:21]=[C:20]([C:22]([F:24])([F:23])[F:25])[CH:19]=2)=[O:48])=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 204431481,4-Dioxane hydrochlorideHCID 866240403-(3,5-Bis(trifluoromethyl)benzyloxy)-2-phenylpropylamine hydrochloride

Product 1

HCID 866240544-amino-N-[3-(3,5-bis(trifluoromethyl)benzyloxy)-2-ph enylpropyl]benzamide hydrochlorideYield 65%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Compound 67 (1.10 g, 923%) was produced as an oily product from 4-tert-butoxycarbonylaminobenzoic acid (0.57 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. After that, Compound 67 (0.95 g, 1.6 mmol) was dissolved in dioxane (2.4 mL), 4 mol/L hydrogen chloride/dioxane (2.4 mL) was added thereto and the mixture was stirred for 20 hours at room temperature. The crystals produced after evaporation of the solvent therefrom in vacuo were filtered from petroleum ether to give Compound 61 (0.55 g, 65%).

Workup

  1. customThe crystals produced
  2. customafter evaporation of the solvent
  3. filtrationin vacuo were filtered from petroleum ether

Sources & evidence

ORD record
ord-0c031bac82e947dd84918c547fca1f50
Source dataset
uspto-grants-2011_05
Patent number
US07939552B2

Reaction notes

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