Phosgene → HCID 19996229, compound

HRID 1381488Notes

Reaction equation

HRID 1381488 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. λmax 1775 cm.-1 and 1700 cm.-1.

Workup

  1. customThe reaction mixture was protected from atmospheric moisture (drying tube)
  2. additionkept at ambient temperature in a water bath during the addition
  3. additionWhen the addition
  4. filtrationwas filtered
  5. washthe solid residue washed with toluene (ca. 50 ml.)
  6. 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-606ae2452647446f941aabcda3664afd
Source dataset
uspto-grants-1989_02
Patent number
US04803201

Reaction notes

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