Dimethylformamide → HCID 69419456, compound

HRID 457771Notes

Reaction equation

HRID 457771 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[NH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][C:19]([C:23]([NH2:25])=[O:24])=[CH:18][CH:17]=3)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].BrC[O:30][C:31](=O)[CH3:32].[CH3:34]N(C=O)C>>[CH3:34][CH2:32][C:31]([NH:25][C:23]([C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([N:11]1[CH2:10][CH2:9][CH:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:13][CH2:12]1)=[CH:22]2)=[O:24])=[O:30]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 68536Bromomethyl acetateHCID 54483006HCID 54483006, compound

Product 1

HCID 69419456HCID 69419456, compoundYield 92%

Conditions

Temperature
0 °C

Procedure

1.95 g (6.13 mmol) of 4-benzylpiperidinyl indole-5-carboxamide was dissolved in 30 mL dry DMF and was treated with 320 mg (8 mmol, 60% suspension in oil) sodium hydride for 30 minutes. The reaction mixture was cooled to 0° C. and 1.225 g (8 mmol) bromomethylacetate was added and stirring continued for 1 h at 0° C. The ice-bath was removed and stirring continued for another 6 h at room temperature. The reaction was quenched by the addition of sat. ammonium chloride solution, diluted with water and extracted with dichloromethane. The extract was dried, evaporated and the residue purified by column chromatography on silica gel eluting with ethylacetate-hexane (25–35% ethylacetate) to yield 2.2 g (92%) of the desired product. MS: M+, 390; M+−1, 389. 1HNMR (CDCl3): □ 7.7 (s, 1H); 7.35–7.1 (m, 8H); 6.6 (s, 1H); 5.1 (s, 2H); 3.75 (s, 3H); 3.0–2.7 (br, m, 4H); 2.6 (d, 2H); 1.9–1.2 9m, 5H).

Workup

  1. customThe ice-bath was removed
  2. stirringstirring
  3. waitcontinued for another 6 h at room temperature
  4. customThe reaction was quenched by the addition of sat. ammonium chloride solution
  5. additiondiluted with water
  6. extractionextracted with dichloromethane
  7. customThe extract was dried
  8. customevaporated
  9. customthe residue purified by column chromatography on silica gel eluting with ethylacetate-hexane (25–35% ethylacetate)

Sources & evidence

ORD record
ord-d850aed22aac45e5bf14c1786e7a1ba3
Source dataset
uspto-grants-2007_03
Patent number
US07189739B2

Reaction notes

Loading…