1-(2-Hydroxyethyl)piperazine → HCID 71087171, compound

HRID 2038177Notes

Reaction equation

[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:19][CH3:20])[N:12]2[CH2:15][CH2:16][CH2:17]Cl)=[C:8]([NH2:21])[N:7]=1)[CH2:2][CH2:3][CH3:4].CCN(C(C)C)C(C)C.[N:31]1([CH2:37][CH2:38][OH:39])[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1>C(#N)C>[NH2:21][C:8]1[N:7]=[C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])[N:14]=[C:13]2[C:9]=1[N:10]=[C:11]([O:19][CH3:20])[N:12]2[CH2:15][CH2:16][CH2:17][N:34]1[CH2:35][CH2:36][N:31]([CH2:37][CH2:38][OH:39])[CH2:32][CH2:33]1

Participants

Conditions

Temperature: 70 °C

Procedure

2-(Butyloxy)-9-(3-chloropropyl)-8-(methyloxy)-9H-purin-6-amine (for example, as prepared for Intermediate 39) (80 mg, 0.255 mmol), DIPEA (0.134 mL, 0.765 mmol) and 2-(1-piperazinyl)ethanol (commercially available, for example, from Aldrich) (133 mg, 1.020 mmol) was heated in acetonitrile (2 mL) in a test-tube in a Radley greenhouse. The reaction was heated at 70° C. for 28 hours then allowed to cool and evaporated in vacuo. Aqueous sodium bicarbonate was added and the mixture was extracted several times with chloroform, the chloroform being filtered through a hydrophobic frit separator. The solvent was removed to give a brown gum (171 mg) which was purified on MDAP (method A). The fractions were evaporated in vacuo and the residue worked up with an aqueous sodium bicarbonate/chloroform extraction as before and the solvent removed to give the title compound as a colourless oil (80 mg).

Workup

temperatureto cool
customevaporated in vacuo
additionAqueous sodium bicarbonate was added
extractionthe mixture was extracted several times with chloroform
filtrationthe chloroform being filtered through a hydrophobic frit separator
customThe solvent was removed

Sources & evidence

ORD record: ord-3649cc4278eb469eb21766956525b9b1
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575340B2

Reaction notes

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