Hydrochloric Acid → HCID 9969778, compound

HRID 1582452Notes

Reaction equation

HRID 1582452 reaction equation
[CH2:1]([N:8]1[CH2:21][CH2:20][C:12]2=[CH:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[N:11]2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22](Cl)(=[O:26])[C:23](Cl)=[O:24].Cl.[CH3:29][CH2:30][O:31]CC>C(N(CC)CC)C>[CH2:1]([N:8]1[CH2:21][CH2:20][C:12]2=[C:13]([C:22](=[O:26])[C:23]([O:31][CH2:30][CH3:29])=[O:24])[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[N:11]2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 65578Oxalyl chlorideHCID 9965406HCID 9965406, compound

Product 1

HCID 9969778HCID 9969778, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent2×

Procedure

(Chart D, Step 1): A round bottom flask is charged with 3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole (1.17 g, 4.23 mmol) and ethyl ether (21 mL). The yellow homogeneous solution is cooled with an ice bath for 10 minutes. Oxalyl chloride (0.37 mL, 4.23 mmol) is added drop-wise. A yellow precipitate is observed, turning into a gel. After 10 minutes of stirring the ether is removed under reduced pressure. Ethanol (21 mL) is quickly added to the yellow residue and a nitrogen stream is established on the surface of the reaction to remove excess HCl. Using a syringe, triethylamine (1.30 mL, 9.31 mmol) is added dropwise forming HCl gas which is carried away by the nitrogen stream. After the triethylamine addition is complete, the flask is adapted with a reflux condenser, and the reaction is heated to reflux for two hours. The reaction is then cooled and concentrated to 2.79 g of a yellow solid. The crude solid is purified on silica gel using a gradient from 25% to 50% ethyl acetate/heptane as the eluent to give 1.293 grams of ethyl 2-(3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-2-oxoacetate as a yellow solid. Anal. Calculated for C23H24N2O3: C, 73.38; H, 6.43; N, 7.44. Found; C, 73.02; H, 6.55; N, 7.38.

Workup

  1. temperatureThe yellow homogeneous solution is cooled with an ice bath for 10 minutes
  2. customis removed under reduced pressure
  3. additionEthanol (21 mL) is quickly added to the yellow residue
  4. customa nitrogen stream is established on the surface of the reaction
  5. customto remove excess HCl
  6. customthe flask is adapted with a reflux condenser
  7. temperaturethe reaction is heated
  8. temperatureto reflux for two hours
  9. temperatureThe reaction is then cooled
  10. concentrationconcentrated to 2.79 g of a yellow solid
  11. customThe crude solid is purified on silica gel using a gradient from 25% to 50% ethyl acetate/heptane as the eluent

Sources & evidence

ORD record
ord-4022ab25dd3644859a276cac5c474f89
Source dataset
uspto-grants-2004_05
Patent number
US06734301B2

Reaction notes

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