Sodium Cyanide → 1-[1-(4-Fluorophenethyl)piperdin-4-yl]-6-cyanomethylindoline

HRID 1790457Notes

Reaction equation

HRID 1790457 reaction equation
[C-:1]#[N:2].[Na+].[F:4][C:5]1[CH:29]=[CH:28][C:8]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([CH2:26]Cl)[CH:24]=4)[CH2:19][CH2:18]3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1>CS(C)=O>[F:4][C:5]1[CH:29]=[CH:28][C:8]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([CH2:26][C:1]#[N:2])[CH:24]=4)[CH2:19][CH2:18]3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 220382531-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-chloromethylindoline

Product 1

HCID 220381751-[1-(4-Fluorophenethyl)piperdin-4-yl]-6-cyanomethylindolineYield 98.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Dimethyl sulfoxide (500 ml) and sodium cyanide (9.8 g) were added to 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-chloromethylindoline (about 70 g) and the resultant mixture was stirred at 50° C. for 2 hr. Next, ice water (500 ml) was added to the reaction solution followed by vigorously stirring. The resulting crystals were collected by filtration, washed with water and air-dried at 80° C. to give the title compound (67 g) as a pale yellow powder (yield: 93%).

Workup

  1. filtrationThe resulting crystals were collected by filtration
  2. washwashed with water
  3. customair-dried at 80° C.

Sources & evidence

ORD record
ord-b2e13b913e8d4084bce170b6149d6a66
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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