Tert-Butylamine → (But-3-yn-1-yl)(tert-butyl)amine

HRID 1984082Notes

Reaction equation

HRID 1984082 reaction equation
C(OS([C:9]1[CH:14]=[CH:13][C:12](C)=CC=1)(=O)=O)CC#C.[C:16]([NH2:20])([CH3:19])([CH3:18])[CH3:17]>CCOCC>[C:16]([NH:20][CH2:9][CH2:14][C:13]#[CH:12])([CH3:19])([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 2720203-Butynyl p-toluenesulfonate

Product 1

HCID 13756229(But-3-yn-1-yl)(tert-butyl)amine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of toluene-4-sulfonic acid but-3-ynyl ester (1.57 g, 7.1 mmol) in tert-BuNH2 (3.54 g. 48 mmol) was heated to reflux for 18 h. The reaction mixture was diluted with Et2O (20 mL), filtered, and concentrated to afford the title product. 1H NMR (CDCl3) δ 2.74 (t, 2H), 2.38 (td, 2H), 2.00 (t, 1H), 1.12 (s, 9H).

Workup

  1. temperatureto reflux for 18 h
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6c8354c35fc24ee080d045855df1caf4
Source dataset
uspto-grants-2009_06
Patent number
US07544672B2

Reaction notes

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