Diisopropylethylamine → HCID 10177192, compound

HRID 2054139Notes

Reaction equation

HRID 2054139 reaction equation
[CH:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:16]1[CH:17]=[CH:18][N:19]2[CH2:25][C:24]3[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=3[NH:22][CH2:21][C:20]=12.C(N(CC)C(C)C)(C)C>S(Cl)(Cl)=O.ClCCl>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:11]([N:22]3[C:23]4[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=4[CH2:25][N:19]4[CH:18]=[CH:17][CH:16]=[C:20]4[CH2:21]3)=[O:13])=[CH:14][CH:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 883374-Cyclohexylbenzoic acidHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine

Product 1

HCID 10177192HCID 10177192, compoundYield 66.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 24386Thionyl ChlorideSolvent

Procedure

A suspension of 4-cyclohexylbenzoic acid (0.50 g, 2.45 mmol) in thionyl chloride (3 mL) was heated at reflux for 30 minutes. After cooling, the thionyl chloride was removed in vacuo. The residue was dissolved in toluene and concentrated in vacuo to give the crude acid chloride as a yellow oil. The acid chloride was then dissolved in dichloromethane (5 mL) and slowly added to a solution of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.67 g, 3.64 mmol) and N,N-diisopropylethyl amine (0.94 mL, 5.4 mmol) in dichloromethane (15 mL). After stirring for 2 hours, the reaction was quenched with water. The layers were separated, and the organic layer was washed with 1 N hydrochloric acid, 1 N sodium hydroxide and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give a yellow oil. Purification by flash chromatography using a solvent system of 50% dichloromethane in hexane followed by 25% ethyl acetate in hexane, gave a white foam which crystallized upon sonication from hexane/ethyl acetate to provide the title compound (0.60 g, 66.1%) as a white solid, mp 127-129° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 minutes
  3. temperatureAfter cooling
  4. customthe thionyl chloride was removed in vacuo
  5. dissolutionThe residue was dissolved in toluene
  6. concentrationconcentrated in vacuo
  7. customto give the crude acid chloride as a yellow oil
  8. customthe reaction was quenched with water
  9. customThe layers were separated
  10. washthe organic layer was washed with 1 N hydrochloric acid, 1 N sodium hydroxide and brine
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo
  14. customto give a yellow oil
  15. customPurification by flash chromatography
  16. customgave a white foam which
  17. customcrystallized upon sonication from hexane/ethyl acetate

Sources & evidence

ORD record
ord-d970e27069274fe3831dcd4a0ce8e9b9
Source dataset
uspto-grants-2008_02
Patent number
US07329653B2

Reaction notes

Loading…