Water → 86928-09-8

HRID 371089Notes

Reaction equation

HRID 371089 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].O.[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1>C(Cl)(Cl)Cl>[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([N:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)=[O:21])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 85014-Chlorobenzoyl chlorideHCID 11430Potassium CarbonateHCID 79341Piperidin-4-ol

Product 1

HCID 1445663686928-09-8

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

30 g (0.296 mol) of 4-hydroxypiperidine, 260 ml of CHCl3, 57.3 g (0.414 mol) of K2CO3 and 260 ml of water are placed in a one liter Erlenmeyer flask, 51.8 g (0.296 mol) of p-chlorobenzoyl chloride, dissolved in 50 ml of CHCl3, are added in the course of 15 minutes, whilst cooling with a bath of iced water. The mixture is stirred overnight at ambient temperature. The organic phase is decanted, the aqueous phase is extracted with CHCl3 and the CHCl3 extract is washed with water until the pH is 6-7. It is dried over MgSO4, filtered and concentrated. The product is recrystallised from ethyl acetate.

Workup

  1. additionare added in the course of 15 minutes
  2. customThe organic phase is decanted
  3. extractionthe aqueous phase is extracted with CHCl3
  4. extractionthe CHCl3 extract
  5. washis washed with water until the pH is 6-7
  6. dry with materialIt is dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe product is recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-44e062a3660f4397b6d9038dad419f75
Source dataset
uspto-grants-1985_07
Patent number
US04529730

Reaction notes

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