Phenethylamine → HCID 23505567, compound

HRID 1884533Notes

Reaction equation

HRID 1884533 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][C:3]=1[CH3:15].BrN1C(=O)CCC1=O.[CH:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][NH2:32])=[CH:26][CH:25]=1>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:7])=[CH:4][C:3]=1[CH2:15][NH:32][CH2:31][CH2:30][C:27]1[CH:28]=[CH:29][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 1001PhenethylamineHCID 67184N-bromobutanimideHCID 11042021Tert-butyl 4-fluoro-3-methylbenzoate

Product 1

HCID 23505567HCID 23505567, compoundYield 64.6%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

According to the procedure of Preparation 4 (b), except using tert-butyl 4-fluoro-3-methylbenzoate (6.25 g, 29.7 mmole), N-bromosuccinimide (5.75 g, 32.3 mmole), benzoyl peroxide (375 mg, 1.6 mmole), CCl4 (50 mL), and 2-phenethylamine (19 mL, 151 mmole), the title compound (6.32 g, 64%) was prepared as a yellow oil following flash chromatography on silica gel (gradient: 20-40% EtOAc/hexanes): MS (ES) m/e 330.1 (M+H)+.

Sources & evidence

ORD record
ord-31129b404b5e4c07a0049a6512ce89ae
Source dataset
uspto-grants-2004_07
Patent number
US06765005B2

Reaction notes

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