Triethylamine → HCID 13108113, compound

HRID 544250Notes

Reaction equation

HRID 544250 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:22]=[C:23]1[O:27][C:25](=[O:26])[CH2:24]1>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:25](=[O:26])[CH2:24][C:23]([CH3:22])=[O:27])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12661DiketeneHCID 784611-Benzylpiperidin-4-ol

Product 1

HCID 13108113HCID 13108113, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 10.0 g of 1-benzyl-4-hydroxypiperidine and a catalytic amount of triethylamine in 10 ml of THF was added dropwise 4.62 g of diketene over 15 minutes. After the addition, the reaction was effected at room temperature for 1.5 hours and then at 50°-60° C. for 4.5 hours. The reaction mixture was concentrated, and then distilled under reduced pressure to obtain 7.20 g of acetoacetic acid-N-benzyl-4-piperidinyl ester (yield: 50.0%), b.p. 146° C./0.13 mmHg.

Workup

  1. additionAfter the addition
  2. waitat 50°-60° C. for 4.5 hours
  3. concentrationThe reaction mixture was concentrated
  4. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-f4649c025e9842fba6111a1fa78b4782
Source dataset
uspto-grants-1984_05
Patent number
US04448964

Reaction notes

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