Phenethyl bromide → N-{(1R)-2-methyl-1-[(2-phenylethoxy)methyl]propyl}-4-(trifluoromethyl)aniline

HRID 1360394Notes

Reaction equation

[CH3:1][CH:2]([CH3:17])[C@@H:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)[CH2:4][OH:5].[CH2:18](Br)[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC=CC=1>[CH3:1][CH:2]([CH3:17])[C@@H:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:14])([F:15])[F:16])=[CH:9][CH:8]=1)[CH2:4][O:5][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 50 °C

Procedure

(2R)-3-Methyl-2-{[4-(trifluoromethyl)phenyl]amino}butan-1-ol (50 mg, 0.201 mmol), which is the compound obtained in Step 1 of Example 2, phenethylbromide (0.22 mL, 2.01 mmol) and tetrabutylammonium hydrogensulfate (catalytic amount) were added to a mixed solvent of benzene(1 mL) and 50% aqueous sodium hydroxide solution (1 mL), and the mixture was stirred at 50° C. for 2 days. After work-up according to a conventional method, the mixture was purified by purification step A to give the title compound (4.76 mg).

Workup

customthe mixture was purified by purification step A

Sources & evidence

ORD record: ord-a912ece6d5cd4024806e16fc1d201bd8
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879863B2

Reaction notes

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