Diisopropylethylamine → HCID 59814692, compound

HRID 2117044Notes

Reaction equation

HRID 2117044 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:16]3[CH2:22][CH:21]4[N:23](C)[CH:18]([CH2:19][CH2:20]4)[CH2:17]3)[C:7]3[C:12]([S:13][C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.ClC(OC(Cl)C)=O.C(N(C(C)C)CC)(C)C>ClCCCl>[CH:21]12[NH:23][CH:18]([CH2:19][CH2:20]1)[CH2:17][CH:16]([N:6]1[C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:15][C:14]=3[S:13][C:12]3[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:22]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5213051-Chloroethyl chloroformateHCID 59814732HCID 59814732, compound2×

Product 1

HCID 59814692HCID 59814692, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 3-bromo-10-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenothiazine, 3i (1.0 g, 2.49 mmol) in 1,2-dichloroethane (15 mL) were added 1-chloroethyl chloroformate (807 μL, 7.5 mmol) and N,N-diisopropyl-N-ethylamine (1.4 mL, 7.97 mmol). The mixture was heated to reflux for 2.5 h, allowed to cool to rt, and evaporated. The mixture was evaporated and the residue was dissolved dissolved in methanol (15 mL) and heated to reflux for 1 h. After work-up, the residue was purified via flash column chromatography (eluent gradient: 0 to 30% MeOH in EtOAc containing 1% triethylamine) to yield 150 mg of recovered starting material 3i and 382 mg (66%) of title compound 3-bromo-10-piperidin-4-yl-10H-phenothiazine, 4i as a mixture of endo and exo isomers. MS m/z (MH+) 387.1/389.1.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2.5 h
  3. customevaporated
  4. customThe mixture was evaporated
  5. dissolutionthe residue was dissolved
  6. dissolutiondissolved in methanol (15 mL)
  7. temperatureheated
  8. temperatureto reflux for 1 h
  9. customAfter work-up, the residue was purified via flash column chromatography (eluent gradient: 0 to 30% MeOH in EtOAc containing 1% triethylamine)
  10. customto yield 150 mg
  11. customof recovered
  12. additionas a mixture of endo and exo isomers

Sources & evidence

ORD record
ord-a2fe821948e94590abc0a515990fb927
Source dataset
uspto-grants-2008_10
Patent number
US07439239B2

Reaction notes

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