Methylamine → HCID 67625240, compound

HRID 863580Notes

Reaction equation

HRID 863580 reaction equation
O[CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]1[CH:14]=[CH:15][C:16]1[CH:20]=[CH:19][S:18][CH:17]=1.[N:21]1C(C)=CC=C[C:22]=1C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.CN>C(Cl)Cl>[CH3:22][NH:21][CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]1[CH:14]=[CH:15][C:16]1[CH:20]=[CH:19][S:18][CH:17]=1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydrideHCID 67625580HCID 67625580, compound

Product 1

HCID 67625240HCID 67625240, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-(3-hydroxypropyl)-2-[2-(thiophen-3-yl)vinyl]indole (121 mg) in 3 ml of methylene chloride was treated with 120 μl of 2,6-lutidine and cooled to 0° C. Trifluoromethanesulfonic anhydride (100 μl) was added, and after stirring for 30 minutes 5 ml of 40% aqueous methylamine was introduced, and the reaction mixture stirred at 25° C. for 3 hours. After stirring for a further 12 hours at 0° C., the reaction mixture was partitioned between methylene chloride and water, the organic layer dried, and solvent was removed under reduced pressure. Preparative TLC on silica gel (eluting with 10% methanol/methylene chloride) gave 83 mg of 1-[3-(methylamino)propyl)-2-[2-(thiophen-3-yl)vinyl]indole (67%). This product was dissolved in 3 ml of methylene chloride containing 150 μl of pyridine and trifluoracetic anhydride (40 μl) was added. After 30 minutes, the mixture was partitioned between diethylether and aqueous sodium bicarbonate, the organic layer dried, and solvent was removed under reduced pressure. Preparative TLC on silica gel (eluting with 3:1 hexane/EtOAc) gave 80 mg of 1-[3-(N-methyltrifluoromethylacetamido)propyl)-2-[2-(thiophen-3-yl)vinyl]indole (73%).

Workup

  1. additionwas introduced
  2. stirringAfter stirring for a further 12 hours at 0° C.
  3. customthe reaction mixture was partitioned between methylene chloride and water
  4. customthe organic layer dried
  5. customsolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-427ba4430d5449b3be1a69abe4db1802
Source dataset
uspto-grants-1998_02
Patent number
US05721267

Reaction notes

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