N-(1,1-Dimethylethyl)benzenemethanamine → HCID 20458608, compound

HRID 544751

Reaction equation

HRID 544751 reaction equation
C(NC(OC1C=C(C(=O)C[Br:21])C=C(OC(=O)NCC)C=1)=O)C.[CH2:23]([NH:30][C:31]([CH3:34])([CH3:33])[CH3:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CC(C)=O>[BrH:21].[CH2:23]([NH:30][C:31]([CH3:34])([CH3:33])[CH3:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 76908N-(1,1-Dimethylethyl)benzenemethanamineHCID 204586013',5'-bis-(N-ethylcarbamoyloxy)-2-bromo acetophenone

Product 1

HCID 20458608HCID 20458608, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 8.0 g of 3',5'-bis-(N-ethylcarbamoyloxy)-2-bromo acetophenone in 100 ml of acetone was added 7.0 g of N-benzyl-t-butylamine. The mixture was refluxed for 18 hours. The 4.1 g of N-benzyl-t-butylamine hydrobromide formed and precipitated during the reaction was filtered off and the filtrate was acidified with conc. HCl. The filtrate was now evaporated to dryness and the title compound was isolated by column chromatography on Silica gel 60 using (1) CHCl3 /ethanol (2:1), (2) ethanol as eluants. The title compound was eluted in the ethanol fraction and recrystallized from ethanol/diethylether. The identity of the product was confirmed with NMR.

Workup

  1. temperatureThe mixture was refluxed for 18 hours

Sources & evidence

ORD record
ord-7fe92459100740a0b008c2a568a04930
Source dataset
uspto-grants-1984_05
Patent number
US04451663

Linked notes

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