Water → HCID 67229818, compound

HRID 1367656Notes

Reaction equation

HRID 1367656 reaction equation
[OH:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]=[CH:10][C:11]1[N:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:19](=[O:27])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:35][CH2:36][N:37]([CH2:40][CH3:41])[CH2:38][CH3:39].O>CN(C=O)C>[CH2:36]([N:37]([CH2:40][CH3:41])[CH2:38][CH2:39][O:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]=[CH:10][C:11]1[N:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:19](=[O:27])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1)[CH3:35]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 13364Diethylaminoethyl chlorideHCID 136400711HCID 136400711, compound

Product 1

HCID 67229818HCID 67229818, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 75 (0.85 g, 0.023 mol) and K2CO3 (0.45 g, 0.003 mol) in DMF (5 mL) was added (2-chloro-ethyl)-diethyl-amine (0.37 g, 0.025 mol). The reaction mixture was stirred at RT for 10 hours, poured into water. The precipitate formed was filtered off, washed with water and purified by column chromatography on silica gel using EtOAc/hexane 1:4 as eluent to yield 76 (0.14 g, 15%). M. Wt. 455. LCMS [M+H]+=456.

Workup

  1. customThe precipitate formed
  2. filtrationwas filtered off
  3. washwashed with water
  4. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-dfa01a54eed141a6819bc3c86c9d2b55
Source dataset
uspto-grants-2011_02
Patent number
US07893260B2

Reaction notes

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