Hydrochloric Acid → Hydrochloric Acid

HRID 551153Notes

Reaction equation

HRID 551153 reaction equation
[C:1]([C:3]1([CH2:16][CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH2:8][CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5][CH2:4]1)#[N:2].C(OCC)C.[ClH:28].O1CCOCC1>CO>[Cl-:28].[C:1]([C:3]1([CH2:16][CH:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)[CH2:8][CH2:7][NH2+:6][CH2:5][CH2:4]1)#[N:2].[ClH:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 57931196HCID 57931196, compound

Product 2

HCID 313Hydrochloric AcidHCID 67173445HCID 67173445, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a round bottom flask was placed tert-butyl 4-cyano-4-(tetrahydro-2H-pyran-4-ylmethyl)piperidine-1-carboxylate (8) (5 g, 16.21 mmol), diethyl ether (200 ml), and methanol (1 ml). To this was added commercially available HCl in dioxane (4M, 0.985 ml, 32.4 mmol.). The solution was stirred overnight. A fine white solid was formed in suspension and filtered with a medium frit to give 4-cyano-4-(tetrahydro-2H-pyran-4-ylmethyl)piperidinium chloride (9) as an HCl salt in quantitative yield after washing with diethyl ether (3×50 ml). MS 209 (M+1)

Workup

  1. customIn a round bottom flask was placed
  2. customA fine white solid was formed in suspension
  3. filtrationfiltered with a medium frit

Sources & evidence

ORD record
ord-37f5ebef8d4e440ebb7acc0c670ee599
Source dataset
uspto-grants-2011_05
Patent number
US07947714B2

Reaction notes

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