Triethylamine → 2-(chloromethyl)-5,6,7,8-tetrahydroquinazolin-4(3H)-one

HRID 713399Notes

Reaction equation

HRID 713399 reaction equation
CCO[C:4]([CH:6]1[C:11](=O)[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].Cl.[Cl:14][CH2:15][C:16]([NH2:18])=[NH:17].C(N(CC)CC)C>CO>[Cl:14][CH2:15][C:16]1[NH:18][C:4](=[O:5])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[N:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 27769572-Chloroacetamidine monohydrochloride

Product 1

HCID 1354490022-(chloromethyl)-5,6,7,8-tetrahydroquinazolin-4(3H)-oneYield 13%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-cyclohexanone-carboxylate (5.5 g, 32 mmol) in methanol was added chloroacetamidine hydrochloride (4.2 g, 32 mmol) and triethylamine (14 mL, 97 mmol). The mixture was stirred at ambient temperature for 60 h. It was then concentrated under reduced pressure and purified via flash column chromatography (ethyl acetate:hexane, 10:90 to 100:0) to provide product (0.82 g, 13% yield). 1H NMR (400 MHz, CD3OD) δ 4.40 (s, 2H), 2.61 (t, J=6.3 Hz, 2H), 2.45 (t, J=6.3 Hz, 2H), 1.68-1.87 (m, 4H). MS m/z 199.2 (M+1), retention time=0.94 min.

Workup

  1. concentrationIt was then concentrated under reduced pressure
  2. custompurified via flash column chromatography (ethyl acetate:hexane, 10:90 to 100:0)

Sources & evidence

ORD record
ord-15e0a2eb507c40eba1e3825117b3276c
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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