Triethylamine → 3-Phenyliminohexahydro-3H-oxazolo[3,4-a]pyridine

HRID 654400Notes

Reaction equation

HRID 654400 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([N:7]=[C:8](Cl)Cl)=[CH:3][CH:2]=1.C(N(CC)CC)C.[OH:18][CH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][NH:21]1>C(Cl)Cl>[C:4]1([N:7]=[C:8]2[N:21]3[CH2:22][CH2:23][CH2:24][CH2:25][CH:20]3[CH2:19][O:18]2)[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12145Phenylimidocarbonyl chlorideHCID 94263Piperidin-2-ylmethanol

Product 1

HCID 144419173-Phenyliminohexahydro-3H-oxazolo[3,4-a]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3 g Phenyl isocyanide dichloride in 10 ml methylene chloride was treated at room temperature with a solution of 5.4 ml triethylamine and 1.7 g 2-hydroxymethylpiperidine in 20 ml methylene chloride. After 12 hours at room temperature, the mixture was washed with water, the organic phase was dried over magnesium sulphate, the solvent was distilled and the residue recrystallised from diisopropyl ether.

Workup

  1. washthe mixture was washed with water
  2. dry with materialthe organic phase was dried over magnesium sulphate
  3. distillationthe solvent was distilled
  4. customthe residue recrystallised from diisopropyl ether

Sources & evidence

ORD record
ord-783c1be8ceb944d8b2390e4b3079cd9b
Source dataset
uspto-grants-1992_07
Patent number
US05131946

Reaction notes

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