1-Chloroethyl chloroformate → HCID 11516034, compound

HRID 2114504Notes

Reaction equation

HRID 2114504 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:16]3[CH2:21][CH2:20][N:19](C)[CH2:18][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>ClCCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][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

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 11538047HCID 11538047, compound2×

Product 1

HCID 11516034HCID 11516034, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 3-bromo-10-(1-methylpiperidin-4-yl)-10H-phenothiazine, 4e (0.6 g, 1.6 mmol) in 1,2-dichloroethane (10 mL) was added 1-chloroethyl chloroformate (276 μL, 2.6 mmol). The mixture was heated to reflux for 1 h, allowed to cool to rt, and evaporated. The residue was dissolved in methanol (10 mL) and heated to reflux for 1 h. Treatment with 1-chloroethyl chloroformate was repeated three more times to obtain ⅔ conversion. 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 4e and 382 mg (66%) of title compound 3-bromo-10-piperidin-4-yl-10H-phenothiazine, 5e. MS m/z (MH+) 401.1/403.1.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 h
  3. customevaporated
  4. dissolutionThe residue was dissolved in methanol (10 mL)
  5. temperatureheated
  6. temperatureto reflux for 1 h
  7. customto obtain ⅔ conversion
  8. customAfter work-up, the residue was purified via flash column chromatography (eluent gradient: 0 to 30% MeOH in EtOAc containing 1% triethylamine)
  9. customto yield 150 mg
  10. customof recovered

Sources & evidence

ORD record
ord-42e522256f8142d8bdfaa2be7023d268
Source dataset
uspto-grants-2008_10
Patent number
US07432257B2

Reaction notes

Loading…