3-Hydroxypiperidine → HCID 178501991, compound

HRID 46829

Reaction equation

HRID 46829 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]([O:11][CH3:12])=[O:10])[N+:5]([O-:13])=[C:4]([NH:14][C:15]([O:17][CH3:18])=[O:16])[CH:3]=1.[OH:19][CH:20]1[CH2:25][CH2:24][CH2:23][NH:22][CH2:21]1>C(Cl)Cl>[OH:19][CH:20]1[CH2:25][CH2:24][CH2:23][N:22]([C:2]2[N:7]=[C:6]([NH:8][C:9]([O:11][CH3:12])=[O:10])[N+:5]([O-:13])=[C:4]([NH:14][C:15]([O:17][CH3:18])=[O:16])[CH:3]=2)[CH2:21]1

Participants

4

Reactant 2

HCID 232933-HydroxypiperidineHCID 178501976HCID 178501976, compound

Product 1

HCID 178501991HCID 178501991, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 5.2 g. of dimethyl 6-chloro-2,4-pyrimidine-dicarbamate-3-oxide in 300 ml. of methylene chloride is treated with 12.4 g. of 3-hydroxy-piperidine and stirred for 60 hours under an argon atmosphere. The residue is then filtered off and the filtrate is concentrated, a white precipitate separating out. This precipitate is filtered off and recrystallized from a mixture of methylene chloride and methanol, there being obtained pure dimethyl racemic-6-(3-hydroxy-1-piperidinyl)-2,4-pyrimidine-dicarbamate-3-oxide, having a melting point of 255° C. (decomposition).

Workup

  1. additionA suspension of 5.2 g
  2. filtrationThe residue is then filtered off
  3. concentrationthe filtrate is concentrated
  4. customa white precipitate separating out
  5. filtrationThis precipitate is filtered off
  6. customrecrystallized from a mixture of methylene chloride and methanol, there

Sources & evidence

ORD record
ord-56bf3edfe6914d7d9f4f535c4df26d79
Source dataset
uspto-grants-1979_11
Patent number
US04175190

Linked notes

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