Chloroform → 5-Cyano-2-(3-dipropylaminobutyl)-1-methoxymethoxy-indane

HRID 2080736Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([O:11][CH2:12][O:13][CH3:14])[CH:6]([CH2:15][CH2:16][CH:17]([N:19]([CH2:23][CH2:24][CH3:25])[CH2:20][CH2:21][CH3:22])[CH3:18])[CH2:5]2.C(Cl)(Cl)Cl.[CH3:30][N:31](C=O)C>[C-]#N.[Zn+2].[C-]#N>[C:30]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([O:11][CH2:12][O:13][CH3:14])[CH:6]([CH2:15][CH2:16][CH:17]([N:19]([CH2:23][CH2:24][CH3:25])[CH2:20][CH2:21][CH3:22])[CH3:18])[CH2:5]2)#[N:31]

Participants

Conditions

Temperature: 80 °C

Procedure

The compound (552 mg) obtained in Example 11-8 was dissolved in DMF (1.67 ml) and added with zinc cyanide (94.3 mg) and tetrakistriphenyl phosphine palladium (61.8 mg), followed by stirring at 80° C. for 48 hours. The reaction solution was added with chloroform and washed with a 7% aqueous ammonium solution and a saturated saline solution. The resultant was dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (436.8 mg) as a yellow oily substance.

Workup

washwashed with a 7% aqueous ammonium solution
dry with materialThe resultant was dried with anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record: ord-38326d74f5ef465eaee0eeab25ca7ae5
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932281B2

Reaction notes

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