Dimethylformamide → HCID 131715617, compound

HRID 580394Notes

Reaction equation

HRID 580394 reaction equation
CO[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:15][C:14]2[CH:16]=[C:17]([C:20]([F:23])([F:22])[F:21])[CH:18]=[CH:19][C:13]=2[NH:12][C:11](=[O:24])[CH:10]1[CH3:25].[H-].[Na+].[CH3:28][N:29]([CH2:31][CH2:32][Cl:33])[CH3:30].CN(C)[CH:36]=[O:37]>>[ClH:33].[CH3:28][N:29]([CH3:30])[CH2:31][CH2:32][N:12]1[C:13]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:16][C:14]=2[CH2:15][C@H:9]([C:4]2[CH:5]=[CH:6][C:7]([O:37][CH3:36])=[CH:8][CH:3]=2)[C@H:10]([CH3:25])[C:11]1=[O:24]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydride2×HCID 20135080HCID 20135080, compound

Product 1

HCID 131715617HCID 131715617, compound

Conditions

Temperature
85 °C

Procedure

To a solution of 1,3,4,5-tetrahydro-4-(methoxyphenyl)-3-methyl-7-(trifluoromethyl)-2H-1-benzazepin-2-one (3.37 g; 9.65 mmole) in dry dimethylformamide 75 ml) was added prewashed (hexane) 50% sodium hydride (5.56 g; 11.58 mmole; 1.2 eq.) with stirring. After ~20 minutes, 1.7N (in toluene) N,N-dimethyl-2-chloroethylamine (24.0 ml; 40.8 mmole) was added, and the mixture was heated at 85° C. for four hours. The mixture was made basic with 50% sodium hydride, and extracted with ethyl acetate (three times). The combined organics were dried (magnesium sulfate) and concentrated, and the dark oily residue was placed under vacuum. The crude material was flash chromatographed (silica gel/1% methanol:dichloromethane, followed by 3% methanol:dichloromethane). The acidified (hydrogen chloride saturated ether) product weighed 1.06 g.

Workup

  1. waitAfter ~20 minutes
  2. extractionextracted with ethyl acetate (three times)
  3. dry with materialThe combined organics were dried (magnesium sulfate)
  4. concentrationconcentrated
  5. customchromatographed (silica gel/1% methanol:dichloromethane, followed by 3% methanol:dichloromethane)

Sources & evidence

ORD record
ord-2cbf7222b4704fe3a3560fd55545b5ed
Source dataset
uspto-grants-1988_06
Patent number
US04752645

Reaction notes

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