Water → HCID 19420484, compound

HRID 1078760Notes

Reaction equation

HRID 1078760 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]#[N:11])=[CH:4][CH:3]=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][C:30]=1[O:31][CH3:32])[CH2:27][NH:26][CH2:25][CH2:24]2.[C:33](=[O:36])([O-])[O-].[K+].[K+].O.CN(C)[CH:42]=[O:43]>>[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][C:30]=1[O:31][CH3:32])[CH2:27][N:26]([C:15]1[CH:14]=[C:13]([CH2:12][C:9]([C:2]3[CH:7]=[CH:6][C:5]([O:43][CH3:42])=[C:4]([O:36][CH3:33])[CH:3]=3)([S:8][C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=3)[C:10]#[N:11])[CH:18]=[CH:17][CH:16]=1)[CH2:25][CH2:24]2

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 156236,7-Dimethoxy-1,2,3,4-TetrahydroisoquinolineHCID 86749757HCID 86749757, compound

Product 1

HCID 19420484HCID 19420484, compound

Conditions

Temperature
85 °C

Procedure

A mixture of 0.21 g of 3-(chloromethyl)-α-3,4-dimethoxyphenyl)-α-[(4-methylphenyl)thio]benzene propane nitrile, 0.091 g of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline and 0.3 g of anhydrous potassium carbonate in 2.0 mL of N,N-dimethylformamide is heated at 85° C. for 4 hours, cooled, poured into water and extracted with ethyl acetate. The ethyl acetate extract is washed with brine, dried and filtered. The filtrate is evaporated in vacuo to yield an oil. This oil is purified by flash chromatography with 1.5% methyl alcohol in chloroform to yield 0.18 g of the desired product as a yellow glassy solid.

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washis washed with brine
  5. customdried
  6. filtrationfiltered
  7. customThe filtrate is evaporated in vacuo
  8. customto yield an oil
  9. customThis oil is purified by flash chromatography with 1.5% methyl alcohol in chloroform

Sources & evidence

ORD record
ord-df3073fa3273485194c726da2c8c0602
Source dataset
uspto-grants-1996_08
Patent number
US05550149

Reaction notes

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