Water → HCID 19420484, compound

HRID 863888Notes

Reaction equation

ClC[C:3]1[CH:4]=[C:5]([CH2:9][C:10]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=2)([S:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[C:11]#[N:12])[CH:6]=[CH:7][CH:8]=1.[CH3:31][O:32][C:33]1[CH:34]=[C:35]2[C:40](=[CH:41][C:42]=1[O:43][CH3:44])[CH2:39][NH:38][CH2:37][CH2:36]2.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:31][O:32][C:33]1[CH:34]=[C:35]2[C:40](=[CH:41][C:42]=1[O:43][CH3:44])[CH2:39][N:38]([C:3]1[CH:4]=[C:5]([CH2:9][C:10]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=3)([S:13][C:14]3[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=3)[C:11]#[N:12])[CH:6]=[CH:7][CH:8]=1)[CH2:37][CH2:36]2

Participants

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. MS(FAB): m/z 595(M+H).

Workup

temperaturecooled
extractionextracted with ethyl acetate
extractionThe ethyl acetate extract
washis washed with brine
customdried
filtrationfiltered
customThe filtrate is evaporated in vacuo
customto yield an oil
customThis oil is purified by flash chromatography with 1.5% methyl alcohol in chloroform

Sources & evidence

ORD record: ord-da28eb71d3ed439b9e691c4ea7bcb72d
Source dataset: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05561141

Reaction notes

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