Diisopropylethylamine → HCID 86676798, compound

HRID 473312Notes

Reaction equation

HRID 473312 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][NH:12][CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][N:32]1[C:40](=[O:41])[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:33]1=[O:42].CCN(C(C)C)C(C)C>CN(C=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]([CH2:13][CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][N:32]2[C:33](=[O:42])[C:34]3[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:40]2=[O:41])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 141120N-(6-Bromohexyl)phthalimideHCID 110566312-(4-Nitrophenoxy)-N-[2-(4-nitrophenyl)ethyl]ethan-1-amine

Product 1

HCID 86676798HCID 86676798, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[2-(4-Nitrophenyl)ethyl]{2-[(4-nitrophenyl)oxy]ethyl}amine (253 mg) and 2-(6-bromohexyl)-1H-isoindole-1,3(2H)-dione (1186 mg) were dissolved in DMF (4 ml) and basified by the addition of DIPEA (0.665 ml). The reaction was stirred for 120 h. The reaction mixture was evaporated to dryness and the residue dissolved in DCM, the solution was absorbed onto a pad of silica and purified on a silica cartridge (12 g) eluting with the following gradient: (A=DCM, B=methanol) t=0 min: B=10%; t=7.5 min: B=0%; t=22.5 min: B=5%. The desired product eluted at ˜15% B (isocratically) and evaporation of the solution to dryness gave the title compound (0.364 g).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionthe residue dissolved in DCM
  3. customthe solution was absorbed onto a pad of silica
  4. custompurified on a silica cartridge (12 g)
  5. washeluting with the following gradient
  6. customt=0 min
  7. customt=7.5 min
  8. customt=22.5 min
  9. washThe desired product eluted at ˜15% B (isocratically) and
  10. customevaporation of the solution to dryness

Sources & evidence

ORD record
ord-4b10f5d740ae402ca8b6048f3da16090
Source dataset
uspto-grants-2014_01
Patent number
US08633319B2

Reaction notes

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