Acetic Anhydride → HCID 10277295, compound

HRID 890612Notes

Reaction equation

HRID 890612 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][NH:12][CH:13]2[CH2:18][CH2:17][C:16]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)([N:19]([CH3:21])[CH3:20])[CH2:15][CH2:14]2)=[CH:2]1.[C:28](OC(=O)C)(=[O:30])[CH3:29]>N1C=CC=CC=1>[CH3:21][N:19]([CH3:20])[C:16]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[CH2:17][CH2:18][CH:13]([N:12]([CH2:11][CH2:10][C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[C:28](=[O:30])[CH3:29])[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 9956432HCID 9956432, compound

Product 1

HCID 10277295HCID 10277295, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N′-[2-(1H-indol-3-yl)ethyl]-N,N-dimethyl-1-pyridin-2-yl cyclohexane-1,4-diamine (250 mg) was dissolved in dry pyridine (5 ml), acetic anhydride (0.64 ml) was added and the mixture was stirred for 22 hours at room temperature. Some ice was added to the reaction mixture and it was then concentrated to low volume. The residue was taken up in 1M sodium hydroxide solution (20 ml) and ethyl acetate (20 ml) and stirred. A white solid was left behind, which could be suction filtered (86 mg). The aqueous phase of the filtrate was extracted with ethyl acetate (2×20 ml). The combined organic extracts were concentrated to low volume after drying. The residue obtained in this way was identical to the solid obtained earlier. Both substances were combined. 219 mg N-(4-dimethylamino-4-pyridin-2-yl cyclohexyl)-N-[2-(1H-indol-3-yl)ethyl] acetamide were obtained (mp 209–210° C.), of which 195 mg were dissolved in 2-butanone (25 ml) with gentle heating to 40° C. and converted into the corresponding dihydrochloride with chlorotrimethyl silane (0.303 ml) (white solid; 219 mg; mp 244–247° C.).

Workup

  1. additionSome ice was added to the reaction mixture and it
  2. concentrationwas then concentrated to low volume
  3. stirringethyl acetate (20 ml) and stirred
  4. waitA white solid was left behind, which
  5. filtrationfiltered (86 mg)
  6. extractionThe aqueous phase of the filtrate was extracted with ethyl acetate (2×20 ml)
  7. concentrationThe combined organic extracts were concentrated to low volume
  8. customafter drying
  9. customThe residue obtained in this way
  10. customobtained earlier

Sources & evidence

ORD record
ord-972af95affc04940ac1a0550f8707819
Source dataset
uspto-grants-2006_02
Patent number
US06998409B2

Reaction notes

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