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

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

Reactant 2

HCID 6385Tert-Butylamine

HCID 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

temperatureto reflux for 4 h
customevaporated
additiondiluted with Et2O
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-278f103381b04ae7aaf078b768d5199a
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093229B2

Reaction notes

Loading…