2-Bromopyridine → HCID 14210569, compound

HRID 2108018Notes

Reaction equation

HRID 2108018 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:9]#[CH:10].C(NCC)C>C(=O)(O)[O-].[Na+]>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:10]#[C:9][CH2:8][O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 79732-BromopyridineHCID 8021DiethylamineHCID 19101838N-Benzyl-6-[(prop-2-yn-1-yl)oxy]hexan-1-amine

Product 1

HCID 14210569HCID 14210569, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 2-bromopyridine (2.0 g), N-[6-[(2-propynyl)oxy]hexyl]benzenemethanamine (3.2 g), BTPC (0.07 g), cuprous iodide (0.007 g), and diethylamine (20 ml) was stirred under nitrogen for 18 h, treated with aqueous sodium bicarbonate (1M, 50 ml), and extracted with diethyl ether (2×100 ml). The dried extract was evaporated and the residue was purified by FCC eluting with diethyl ether to give the title compound as a yellow oil (3.0 g), t.l.c. (diethyl ether) Rf 0.05.

Workup

  1. extractionextracted with diethyl ether (2×100 ml)
  2. extractionThe dried extract
  3. customwas evaporated
  4. customthe residue was purified by FCC
  5. washeluting with diethyl ether

Sources & evidence

ORD record
ord-25aa3b86629d471cab1511dc50933bd8
Source dataset
uspto-grants-1990_06
Patent number
US04937251

Reaction notes

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