Triethylamine → N'-Hydroxy-4-(4-hydroxytetrahydro-2H-pyran-4-yl)benzenecarboximidamide

HRID 2400537Notes

Reaction equation

HRID 2400537 reaction equation
[OH:1][C:2]1([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.Cl.[NH2:17][OH:18].C(N(CC)CC)C>C(O)C>[OH:18][N:17]=[C:12]([C:11]1[CH:10]=[CH:9][C:8]([C:2]2([OH:1])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]2)=[CH:15][CH:14]=1)[NH2:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 595046634-(4-Hydroxytetrahydro-2H-pyran-4-yl)benzenecarbonitrile

Product 1

HCID 76817378N'-Hydroxy-4-(4-hydroxytetrahydro-2H-pyran-4-yl)benzenecarboximidamideYield 119.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-(4-hydroxytetrahydro-2H-pyran-4-yl)benzonitrile (Step 1, 200 mg, 0.984 mmol), hydroxylamine hydrochloride (150 mg, 2.17 mmol) and triethylamine (219 mg, 2.17 mmol) in ethanol (5 mL) was stirred and heated at reflux for 4 h. After being cooled to rt, the reaction mixture as such was subjected to preparative HPLC, affording the pure title compound (278 mg, 99%): 1H NMR (500 MHz, DMSO-d6) δ 9.71 (broad, 1H), 9.58 (s, 1H), 7.62 (d, 2H), 7.48 (d, 2H), 7.22 (broad, 1H), 5.78 (s, 2H), 5.07 (s, 1H), 3.80-3.75 (m, 2H), 3.72-3.68 (m, 2H), 2.00-1.93 (m, 2H), 1.53-1.49 (m, 2H); ES-MS m/z 237 (MH)+; HPLC RT (Method F) 0.72 min.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 h

Sources & evidence

ORD record
ord-f68e514122cc4651a9f42ff5d4efd66f
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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