Triethylamine → HCID 22611425, compound

HRID 1737736Notes

Reaction equation

HRID 1737736 reaction equation
C([O-])C.Cl.Cl.[NH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH:16]1[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]1.C(N(CC)CC)C.[CH3:30][N:31]=[C:32]=[O:33]>ClCCl>[CH3:30][NH:31][C:32]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH:16]1[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]1)=[O:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 86751892HCID 86751892, compound

Product 1

HCID 22611425HCID 22611425, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.0 gm (5.74 mMol) 5-amino-3-(1-methylpiperidin-4-yl)-1H-indole dihydrochloride mono-ethanolate and 5.0 mL (36 mMol) triethylamine in 100 mL dichloromethane were added 0.74 mL (12.6 mMol) methyl isocyanate. The reaction mixture was stirred for 15 minutes and was then washed with 100 mL of water. The remaining organics were dried over sodium sulfate and concentrated under reduced pressure. The resultant residue was crystallized from acetonitrile to give 1.05 gm (64%) of the title compound.

Workup

  1. washwas then washed with 100 mL of water
  2. dry with materialThe remaining organics were dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resultant residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-caee35adb1d14fe8bc60e55c54b0cde2
Source dataset
uspto-grants-1999_10
Patent number
US05962474

Reaction notes

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