Sulfuric Acid → HCID 22097477, compound

HRID 1734566Notes

Reaction equation

HRID 1734566 reaction equation
[OH:1][C:2]1([C:9]#[N:10])[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.S(=O)(=O)(O)[OH:12].C(=O)([O-])[O-].[Ba+2].S([O-])([O-])(=O)=O.[Ba+2]>C(O)C.O>[OH:1][C:2]1([C:9](=[O:12])[NH2:10])[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 10563Barium CarbonateHCID 24414Barium SulfateHCID 2840534-Hydroxy-1-methylpiperidine-4-carbonitrile

Product 1

HCID 22097477HCID 22097477, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The compound 4-hydroxy-4-cyano-1-methylpiperidine (36.4 g, 0.26 mole) was gradually added to sulfuric acid (80 ml), under external cooling. The mixture was maintained at room temperature for 41 hours, then was added to powdered ice (30 g). The resulting solution was neutralized with barium carbonate (376 g) to pH 8-9 and after addition of water the resulting barium sulfate was separated and washed with methanol. The filtrate was concentrated under reduced pressure. The product, 4-hydroxy-4 -carbamoyl-1-methylpiperidine (28.16 g, 0.18 mole, 69% yield), crystallized from ethanol as a white solid (mp. 180° C.).

Workup

  1. customwas separated
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-80fc6d9ce70441f08bed7fca341afaaf
Source dataset
uspto-grants-1996_07
Patent number
US05534520

Reaction notes

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