Diisopropylethylamine → 2-{1-Methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]piperazin-2-yl}ethanol

HRID 518820Notes

Reaction equation

C(N(CC)C(C)C)(C)C.[CH3:10][N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH:12]1[CH2:17][CH2:18][OH:19].F[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[C:23]([O:30][CH:31]([CH3:33])[CH3:32])[CH:22]=1>C(#N)C>[CH3:10][N:11]1[CH2:16][CH2:15][N:14]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[C:23]([O:30][CH:31]([CH3:33])[CH3:32])[CH:22]=2)[CH2:13][CH:12]1[CH2:17][CH2:18][OH:19]

Participants

Conditions

Temperature: 110 °C

Procedure

974 mg of N,N-diisopropylethylamine and 724 mg of 2-(1-methylpiperazin-2-yl)ethanol are added to a suspension of 1 g of 4-fluoro-1-nitro-2-(propan-2-yloxy)benzene in 10 ml of acetonitrile. The reaction medium is microwave-heated at 110° C. for 6 hours and then concentrated to dryness under reduced pressure. Purification is carried out by flash chromatography on silica gel (40-63 microns), elution being carried out with a mixture of dichloromethane and methanol (100/0) to (90/10). 1.15 g of 2-{1-methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]piperazin-2-yl}ethanol are obtained in the form of a yellow oil.

Workup

concentrationconcentrated to dryness under reduced pressure
customPurification
washis carried out by flash chromatography on silica gel (40-63 microns), elution
additionbeing carried out with a mixture of dichloromethane and methanol (100/0) to (90/10)

Sources & evidence

ORD record: ord-86a6b3c2caf745d2ae32a239921986fc
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115140B2

Reaction notes

Loading…