Water → HCID 86744901, compound

HRID 1198149Notes

Reaction equation

HRID 1198149 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.O.[N:10]([C:13]([CH3:18])([CH3:17])[C:14](Cl)=[O:15])=[N+:11]=[N-:12].[OH-].[Na+]>O1CCOCC1>[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:14](=[O:15])[C:13]([N:10]=[N+:11]=[N-:12])([CH3:18])[CH3:17])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 4207714-PiperidinemethanolHCID 11171055HCID 11171055, compound

Product 1

HCID 86744901HCID 86744901, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

15 g. (0.13 mole) 4-Hydroxymethylpiperidine are dissolved in 130 ml. water and 30 ml. dioxan and 19.4 g. (0.13 mole) 2-azido-2-methylpropionic acid chloride (according to analogous literature: J.A.C.S., 77, 112/1955) added dropwise thereto. The pH of the solution is kept at 12 to 12.5 by the simultaneous dropwise addition of 2N aqueous sodium hydroxide solution. After ending of the reaction, the reaction mixture is extracted with diethyl ether. After drying with anhydrous sodium sulphate and evaporating, there are obtained 17.8 g. of crude oil, i.e. 60% of theory, which can be used in the next step without further purification.

Workup

  1. customAfter ending of the reaction
  2. extractionthe reaction mixture is extracted with diethyl ether
  3. dry with materialAfter drying with anhydrous sodium sulphate
  4. customevaporating
  5. customthere are obtained 17.8 g
  6. customof crude oil, i.e. 60% of theory, which can be used in the next step without further purification

Sources & evidence

ORD record
ord-72946d2b232e44e4866191e2963a9cce
Source dataset
uspto-grants-1994_01
Patent number
US05280031

Reaction notes

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