Sulfuric Acid → HCID 22097477, compound

HRID 1458763Notes

Reaction equation

HRID 1458763 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-fa3d022d618d40ff83b8e511ed23dfe5
Source dataset
uspto-grants-1998_12
Patent number
US05852029

Reaction notes

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