Potassium Cyanide → HCID 54536415, compound

HRID 1870249Notes

Reaction equation

I[CH2:2][C@@H:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:6][CH2:5][CH2:4]1.[C-:24]#[N:25].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C)C=O>[C:24]([CH2:2][C@@H:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:6][CH2:5][CH2:4]1)#[N:25]

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of (5S)-5-iodomethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (1.41 g), potassium cyanide (0.42 g), a catalytic amount of 18-crown-6 and dimethylformamide (16 ml) is heated with stirring at 85° C. for one hour. To the mixture is added potassium cyanide (0.42 g), and the mixture is further stirred at 85° C. for totally 6 hours. To the reaction solution is added ice, and the mixture is extracted with ethyl acetate--toluene. The extract is dried over sodium sulfate, and concentrated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=4:1), and recrystallized from ethyl acetate--n-hexane to give (5R)-5-cyanomethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (0.41 g).

Workup

stirringthe mixture is further stirred at 85° C. for totally 6 hours
additionTo the reaction solution is added ice
extractionthe mixture is extracted with ethyl acetate
dry with materialThe extract is dried over sodium sulfate
concentrationconcentrated under reduced pressure
customto remove the solvent
customThe residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=4:1)
customrecrystallized from ethyl acetate

Sources & evidence

ORD record: ord-e4a85dd66ac14169a9192db57be028ca
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06096736

Reaction notes

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