Thionyl Chloride → HCID 13392523, compound

HRID 1607750Notes

Reaction equation

HRID 1607750 reaction equation
O[CH2:2][C:3]1([NH2:10])[CH2:8][CH2:7][CH2:6][NH:5][C:4]1=[O:9].S(Cl)([Cl:13])=O>C(Cl)(Cl)Cl>[ClH:13].[NH2:10][C:3]1([CH2:2][Cl:13])[CH2:8][CH2:7][CH2:6][NH:5][C:4]1=[O:9]

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 13315050HCID 13315050, compound

Product 1

HCID 13392523HCID 13392523, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-hydroxymethyl-3-amino-2-piperidone (7 g or 0.049 mol) in anhydrous dimethylforamamide (50 ml) is added one equivalent of thionyl chloride (3.6 ml). The reaction mixture is stirred at 80° C. under nitrogen. After 24 hours, another equivalent of thionyl chloride (3.6 ml) is added and stirring is continued for 2 hour. Then the solvent is stripped off under reduced pressure. Trituration of the semi-solid residue with chloroform (2×30 ml) leaves 2.1 g of crystalline analytically pure 3-amino-3-chloromethyl-2-piperidone hydrochloride: m.p. 230° C.

Workup

  1. stirringstirring
  2. waitis continued for 2 hour

Sources & evidence

ORD record
ord-c57525b4e2ae48e785a8f96eb6e80434
Source dataset
uspto-grants-1989_09
Patent number
US04866206

Reaction notes

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