Water → HCID 19916988, compound

HRID 1756176Notes

Reaction equation

HRID 1756176 reaction equation
[CH2:1]([N:3]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20]Br)[CH:15]=1)[CH2:4]/[CH:5]=[CH:6]/[C:7]#[C:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH3:2].[C-:22]#[N:23].[Na+].C(OCC)C.O>CN(C)C=O>[CH2:1]([N:3]([CH2:13][C:14]1[CH:15]=[C:16]([CH2:20][C:22]#[N:23])[CH:17]=[CH:18][CH:19]=1)[CH2:4]/[CH:5]=[CH:6]/[C:7]#[C:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 8929Sodium CyanideHCID 19917079HCID 19917079, compound

Product 1

HCID 19916988HCID 19916988, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

240 mg of (E)-N-ethyl-N-(6,6-dimethyl-2-hepten-4-ynyl)-3-bromomethylbenzylamine was dissolved in 4 ml of dimethylformamide, and 61 mg of sodium cyanide was added. The mixture was stirred overnight at room temperature, and then ethyl ether and water were added. The organic layer separated was worked up in a customary manner to give 195 mg of (E)-3-(N-ethyl-6,6-dimethyl-2-hepten-4-ynylaminomethyl)phenylacetonitrile as a colorless oil.

Workup

  1. customThe organic layer separated

Sources & evidence

ORD record
ord-559dab9f5fe1499f9250801765d8f6f1
Source dataset
uspto-grants-1995_08
Patent number
US05439932

Reaction notes

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