Tert-Butylamine → Tert-butyl-pent-4-ynyl-amine

HRID 417856Notes

Reaction equation

HRID 417856 reaction equation
I[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].[C:7]([NH2:11])([CH3:10])([CH3:9])[CH3:8]>>[C:7]([NH:11][CH2:2][CH2:3][CH2:4][C:5]#[CH:6])([CH3:10])([CH3:9])[CH3:8]

Participants

3

Reactant 2

HCID 6385Tert-ButylamineHCID 110197205-Iodo-1-pentyne

Product 1

HCID 57713825Tert-butyl-pent-4-ynyl-amine

Procedure

A solution of 5-iodo-pent-1-yne (1.0 g, 5.2 mmol) in tert-BuNH2 (2.0 g. 27 mmol) was heated to reflux for 4 h, evaporated, diluted with Et2O, filtered, and concentrated to afford the title compound. 1H NMR (CDCl3) δ 2.67 (t, 2H), 2.27 (td, 2H), 1.96 (t, 1H), 1.70 (quint., 2H), 1.11 (s, 9H).

Workup

  1. temperatureto reflux for 4 h
  2. customevaporated
  3. additiondiluted with Et2O
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-278f103381b04ae7aaf078b768d5199a
Source dataset
uspto-grants-2012_01
Patent number
US08093229B2

Reaction notes

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