Dicyanamide → 2-Methyl 3-(1-N-pyrrolidinyl-3-cyanopropyl)pyridine

HRID 27255

Reaction equation

HRID 27255 reaction equation
C1(S([O-])(=O)=O)C=CC=CC=1.C(C[N+:14]1([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22]N=2)[CH2:18][CH2:17][CH2:16][CH2:15]1)#N.Br[CH2:27][CH2:28][C:29]#[N:30].[C:31](NC#N)#[N:32].[BH4-].[Na+]>C(O)C>[CH3:22][C:23]1[C:24]([CH2:25][CH2:20][CH:19]([N:14]2[CH2:15][CH2:16][CH2:17][CH2:18]2)[C:31]#[N:32])=[CH:27][CH:28]=[CH:29][N:30]=1

Participants

6

Reactant 4

HCID 10443DicyanamideHCID 170203-BromopropionitrileHCID 4311764Sodium borohydrideHCID 5458873(1-(2-Pyridinylmethyl)-15-pyrrolidin-1-yl)acetonitrile benzenesulfonate

Product 1

HCID 233444222-Methyl 3-(1-N-pyrrolidinyl-3-cyanopropyl)pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-cyanomethyl-1-(2-picolyl)pyrrolidinium benzenesulfonate (see Preparation II) is rearranged and alkylated with 3-bromopropionitrile as in Example 2. The resulting dicyanoamine is decyanated with sodium borohydride in ethanol to give the product. Purification is effected via the picrate.

Workup

  1. customto give the product
  2. customPurification

Sources & evidence

ORD record
ord-77ed0ada2d654ca3bda0d891202c6bc6
Source dataset
uspto-grants-1980_09
Patent number
US04220781

Linked notes

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