Hydrochloric Acid → N-[4-(trifluoromethyl)benzyl]-N-[4-(3-undecyl-1,2,4-oxadiazol-5-yl)benzyl]amine Hydrochloride

HRID 735831Notes

Reaction equation

[F:1][C:2]([F:42])([F:41])[C:3]1[CH:40]=[CH:39][C:6]([CH2:7][N:8]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[O:27][N:26]=[C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[N:24]=3)=[CH:19][CH:18]=2)C(=O)OC(C)(C)C)=[CH:5][CH:4]=1.[ClH:43]>C(Cl)Cl>[ClH:43].[F:42][C:2]([F:1])([F:41])[C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[O:27][N:26]=[C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[N:24]=3)=[CH:21][CH:22]=2)=[CH:39][CH:40]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cold (0° C.) solution of tert-butyl 4-(trifluoromethyl)benzyl[4-(3-undecyl-1,2,4-oxadiazol-5-yl)benzyl]carbamate (43 mg, 0.07 mmol) in DCM (3 mL) was added a solution of HCl (4N in dioxane, 3 mL) and the resulting reaction mixture was stirred 3 h at 0° C., then 14 h at rt. Evaporation of the solvent gave the title compound as a white powder used in the next steps without further purification (29 mg, 99%). M−(APCI): 486.0; M+(APCI): 488.2 HPLC (Condition A), Rt: 5.4 min (HPLC purity: 82%).

Workup

customthe resulting reaction mixture
custom14 h
customat rt
customEvaporation of the solvent

Sources & evidence

ORD record: ord-3e07826bb32e4a6cb534f21aa23730ee
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592477B2

Reaction notes

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