Tert-Butylamine → HCID 423813, compound

HRID 403591Notes

Reaction equation

HRID 403591 reaction equation
Cl[CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].C([O-])([O-])=O.[K+].[K+].[CH3:18][C:19]([NH2:22])([CH3:21])[CH3:20]>C(#N)C>[C:19]([NH:22][CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5])([CH3:21])([CH3:20])[CH3:18]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 11430Potassium CarbonateHCID 702953-Chloropropiophenone

Product 1

HCID 423813HCID 423813, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-chloro-1-phenylpropan-1-one (5.0 g, 0.03 mol) and K2CO3 (12.4 g, 0.09 mol) in acetonitrile (100 mL) was added 2-methylpropan-2-amine (4.38 g, 0.06 mol), and the reaction mixture was stirred at rt overnight. The solution was filtered, and the filtrate was concentrated to give 3-(tert-butylamino)-1-phenylpropan-1-one (5.89 g, 96%). 1H NMR (CDCl3): 1.01-1.10 (s, 9H), 1.42-1.56 (s, 1H), 2.86-2.92 (m, 2H), 3.09-3.14 (m, 2H), 7.34-7.43 (m, 2H), 7.44-7.51 (m, 1H), 7.85-7.91 (m, 2H).

Workup

  1. filtrationThe solution was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-050baf48f3474906b455a9488060a8b3
Source dataset
uspto-grants-2014_06
Patent number
US08748444B2

Reaction notes

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