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Sodium Cyanide → 1'-(Phenylmethyl)-(1,4'-bipiperidine)-4'-carbonitrile

HRID 377795
Notes
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Reaction equation

HRID 377795 reaction equation
[C-:1]#[N:2].[Na+].[CH2:4]([N:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl.[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>O.CO>[CH2:4]([N:11]1[CH2:16][CH2:15][C:14]([C:1]#[N:2])([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:13][CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 192201-Benzyl-4-piperidoneHCID 2723721Piperidine, hydrochloride (1:1)

Product 1

HCID 27334341'-(Phenylmethyl)-(1,4'-bipiperidine)-4'-carbonitrileYield 95.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 962
Water
Solvent
2×

Procedure

A solution of 5.3 g of sodium cyanide in 20 ml of water is added dropwise at RT to a solution of 18.9 g of 1-benzylpiperid-4-one and 12.16 g of piperidine hydrochloride in 25 ml of MeOH and 25 ml of water and the mixture is stirred for 48 hours at RT. The precipitate formed is filtered off, washed with water and dried under vacuum to give 27 g of the expected product.

Workup

  1. customThe precipitate formed
  2. filtrationis filtered off
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-46985320c2c84f1589a55e8d4035f440
Source dataset
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06028082

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes