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

HRID 1174019
Notes
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Reaction equation

HRID 1174019 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6212ChloroformHCID 6228DimethylformamideHCID 230791615-Bromo-2-(3-dipropylaminobutyl)-1-methoxymethoxy-indane

Product 1

HCID 230792975-Cyano-2-(3-dipropylaminobutyl)-1-methoxymethoxy-indane

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Conditions

Temperature
80 °C

Procedure

The compound (552.4 mg) obtained in Example 127-8 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 saturated saline solution. The solution 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

  1. washwashed with a 7% aqueous ammonium solution and saturated saline solution
  2. dry with materialThe solution was dried with anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-71e2765917dc487f86436de62495e2d5
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07833991B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes