Phosgene → HCID 19996229, compound

HRID 2248389Notes

Reaction equation

HRID 2248389 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[C:27](Cl)([Cl:29])=[O:28]>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:27]([Cl:29])=[O:28])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 2794620Benzyl 4-Hydroxy-1-piperidinecarboxylate

Product 1

HCID 19996229HCID 19996229, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

1-Benzyloxycarbonyl-4-hydroxypiperidine (15 g., 0.0638 mole) and N,N-diisopropylethylamine (12.3 ml., 9.13 g., 0.0707 mole) were dissolved in toluene (150 ml.), and the solution was added over 30 min. to a solution. of phosgene (12.63 g., 0.128 mole) in toluene (150 ml.). The reaction mixture was protected from. atmospheric moisture (drying tube), stirred magnetically, and kept at ambient temperature in a water bath during the addition. When the addition was complete the mixture was filtered and the solid residue washed with toluene (ca. 50 ml.). The solvent in the combined filtrate and washings was evaporated in vacuo (1 mm. pressure, solid CO2 cold finger condenser) to give 1-benzyloxycarbonyl-4-chlorocarbonyloxypiperidine, I.R. λ max 1775cm.-1 and 1700 cm.-1.

Workup

  1. additionthe solution was added over 30 min. to a solution
  2. customatmospheric moisture (drying tube)
  3. additionkept at ambient temperature in a water bath during the addition
  4. additionWhen the addition
  5. filtrationwas filtered
  6. washthe solid residue washed with toluene (ca. 50 ml.)
  7. customThe solvent in the combined filtrate and washings was evaporated in vacuo (1 mm. pressure, solid CO2 cold finger condenser)

Sources & evidence

ORD record
ord-819ccbc19c5948e7ba6c697d67f02fcb
Source dataset
uspto-grants-1991_08
Patent number
US05039710

Reaction notes

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