Hydrochloric Acid → HCID 18700424, compound

HRID 2288984Notes

Reaction equation

HRID 2288984 reaction equation
[NH:1]1[CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1.C=O.[C-]#[N:13].[Na+].Cl.[Cl-].[Na+].[CH2:18](O)[CH3:19]>>[C:18]([CH2:19][N:1]1[CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1)#[N:13]

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 702Ethanol2×HCID 712FormaldehydeHCID 37734-Piperidinecarboxylic acidHCID 5234Sodium ChlorideHCID 8929Sodium Cyanide

Product 1

HCID 18700424HCID 18700424, compound

Procedure

In a 12 l round bottomed flask combine isonipecotic acid (1226 g, 9.49 moles), 37% formaldehyde (850 ml) and absolute ethanol (5.0 l) and stir for thirty minutes. Sodium cyanide (470 g, 9.49 moles) is added and the reaction stirred at ambient temperature overnight. Absolute ethanol (1.3 l) and 12 M hydrochloric acid (795 ml) is added and the suspension stirred for four hours. The product is collected by vacuum filtration, washed thrice with methyl-t-butylether (3.0 l) and dried at 25 in Hg overnight to give N-cyanomethyl isonipecotic acid (1909 g, 8.05 moles) as a 1:1 mixture with sodium chloride. 1H NMR (400 MHz, d6 DMSO) d 1.55 (m, 2H), 1.82 (m, 2H), 2.18 (m, 3H), 2.72 (m, 2H), 3.71 (s, 2H), 12.30 (bs, 1H).

Workup

  1. customIn a 12 l round bottomed flask combine
  2. stirringthe suspension stirred for four hours
  3. filtrationThe product is collected by vacuum filtration
  4. washwashed thrice with methyl-t-butylether (3.0 l)
  5. customdried at 25 in Hg overnight

Sources & evidence

ORD record
ord-05e5b413f7a043d7b0a04e2b59793017
Source dataset
uspto-grants-2000_07
Patent number
US06090825

Reaction notes

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