Benzyl chloroformate → HCID 45358666, compound

HRID 377198Notes

Reaction equation

HRID 377198 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][OH:9].[OH-].[Na+].Cl[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]>O1CCOCC1>[CH2:16]([O:15][C:13]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][OH:9])=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×HCID 151442-Piperidin-2-ylethanol

Product 1

HCID 45358666HCID 45358666, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

2-Piperidine ethanol (39.6 ml, 0.31 mol) was dissolved in 5M aq NaOH (62 ml, 0.31 mol) and dioxan (100 ml). The mixture was cooled to 0° C. and treated with benzyl chloroformate (45.3 ml, 0.32 mol) and 5M NaOH (62 ml, 0.31 mol). Stirring was continued at room temp. for 18 hours. Dioxan was removed in vacuo and the aqueous phase extracted with ether before acidifying with 5N HCl and extracting again with ether. The organic phase was dried and evaporated in vacuo and the residue purified by chromatography on silica gel to give the title compound (77.2 g. 95%). MH+ 264.

Workup

  1. customDioxan was removed in vacuo
  2. extractionthe aqueous phase extracted with ether
  3. extractionextracting again with ether
  4. customThe organic phase was dried
  5. customevaporated in vacuo
  6. customthe residue purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a73adbc824284e41a9fbe67c1543a175
Source dataset
uspto-grants-2000_02
Patent number
US06025367

Reaction notes

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